Global Patent Index - EP 1097143 A1

EP 1097143 A1 2001-05-09 - METHOD FOR PREPARING 5-(1-METHYLETHYL)-6-(PHENYLMETHYL)PYRIMIDINE-2,4(1H,3H)-DIONE

Title (en)

METHOD FOR PREPARING 5-(1-METHYLETHYL)-6-(PHENYLMETHYL)PYRIMIDINE-2,4(1H,3H)-DIONE

Title (de)

VERFAHREN ZUR HERSTELLUNG VON 5-(1-METHYLETHYL) 6-(PHENYLMETHYL)PYRIMIDIN-2,4(1H,3H)-DIONE

Title (fr)

PROCEDE POUR LA PREPARATION DE 5-(1-METHYLETHYL)-6-(PHENYLMETHYL)PYRIMIDINE-2, 4(1H,3H)-DIONE

Publication

EP 1097143 A1 (FR)

Application

EP 99929485 A

Priority

  • FR 9901723 W
  • FR 9809085 A

Abstract (en)

[origin: FR2781219A1] Preparation of 1-alkoxyalkyl-6-benzyl-5-isopropyl-pyrimidine-2,4(1H,3H)-diones (II) involves preparing 5-(phenylmethyl)-4-(1-methylethyl)-pyrimidines (IV) by reacting a 4-chloro-5-(1-methylethyl)-pyrimidine with an organometallic reagent over a homogeneous metal catalyst, then hydrolyzing and alkylating. (IV) are new compounds. Preparation of 1-alkoxyalkyl-5-(1-methylethyl)-6-(phenylmethyl)-pyrimidine-2,4(1H,3H) -diones of formula (II) involves: (a) preparing 5-(phenylmethyl)-4-(1-methylethyl)-pyrimidines of formula (IV) by reacting a 4-chloro-5-(1-methylethyl)-pyrimidine of formula (VI) with an organometallic reagent of formula PhCH2MX (V) (or with a benzyl halide in presence of magnesium), in presence of a homogeneous metal catalyst; (b) converting (IV) into 5-(1-methylethyl)-6-(phenylmethyl)-pyrimidine-2,4(1H,3H)-dione of formula (I) by direct acid hydrolysis or alternatively (if R1 = halo) by dialkoxylation followed by hydrolysis; and (c) alkylating (I). R1 = halo or 1-4C alkoxy; M = alkaline earth metal or other Group II or III metal; X = halo; Ra = 1-6C alkyl; Rb = H or 1-4C alkyl. Independent claims are included for: (1) preparation of (IV) by step (a) as above; (2) preparation of (I) by steps (a) and (b) as above; and (3) intermediates (IV) as new compounds.

IPC 1-7 (main, further and additional classification)

C07D 239/54; C07D 239/30; C07D 239/52

IPC 8 full level (invention and additional information)

C07D 239/30 (2006.01); C07D 239/52 (2006.01); C07D 239/54 (2006.01)

CPC (invention and additional information)

C07D 239/30 (2013.01); C07D 239/52 (2013.01); C07D 239/54 (2013.01)

Citation (search report)

See references of WO 0003999A1

Designated contracting state (EPC)

AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

EPO simple patent family

FR 2781219 A1 20000121; FR 2781219 B1 20000825; AU 4628699 A 20000207; AU 764168 B2 20030814; CA 2337243 A1 20000127; EP 1097143 A1 20010509; JP 2002520400 A 20020709; US 6452006 B1 20020917; WO 0003999 A1 20000127

INPADOC legal status


2004-07-07 [18D] DEEMED TO BE WITHDRAWN

- Effective date: 20040106

2003-10-08 [17Q] FIRST EXAMINATION REPORT

- Effective date: 20030826

2002-11-06 [RAP1] TRANSFER OF RIGHTS OF AN EP PUBLISHED APPLICATION

- Owner name: FINORGA SA

2001-07-11 [RAP1] TRANSFER OF RIGHTS OF AN EP PUBLISHED APPLICATION

- Owner name: SYLACHIM

2001-05-09 [17P] REQUEST FOR EXAMINATION FILED

- Effective date: 20010216

2001-05-09 [AK] DESIGNATED CONTRACTING STATES:

- Kind Code of Ref Document: A1

- Designated State(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

2001-05-09 [AX] REQUEST FOR EXTENSION OF THE EUROPEAN PATENT TO

- Free text: AL PAYMENT 20010216;LT PAYMENT 20010216;LV PAYMENT 20010216;MK PAYMENT 20010216;RO PAYMENT 20010216;SI PAYMENT 20010216