Diisopropylethylamine → 5-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)pyridin-2-amine

HRID 2098587

반응식

HRID 2098587 반응식
[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[N:13][C:14](F)=[CH:15][CH:16]=3)=[CH:8][C:6]=2[N:7]=1.[Cl:24][C:25]1[N:26]=[C:27]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:28]2[CH:33]=[C:32]([C:34]3[CH:35]=[N:36][C:37](F)=[CH:38][CH:39]=3)[S:31][C:29]=2[N:30]=1.C([N:50](C(C)C)CC)(C)C>CN1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[N:13][C:14]([NH2:26])=[CH:15][CH:16]=3)=[CH:8][C:6]=2[N:7]=1.[Cl:24][C:25]1[N:26]=[C:27]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:28]2[CH:33]=[C:32]([C:34]3[CH:35]=[N:36][C:37]([NH2:50])=[CH:38][CH:39]=3)[S:31][C:29]=2[N:30]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 598292882-Chloro-6-(6-fluoropyridin-3-yl)-4-morpholinothieno[3,2-d]pyrimidineHCID 866183712-Chloro-6-(6-fluoropyridin-3-yl)-4-morpholinothieno[2,3-d]pyrimidine

생성물 2

HCID 866183695-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)pyridin-2-amineHCID 866183702-Chloro-6-(6-aminopyridin-3-yl)-4-morpholinothieno[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 84541-Methylpyrrolidine용매

반응 조건

온도
135 °C

실험 절차

A mixture of 2-chloro-6-(6-fluoropyridin-3-yl)-4-morpholinothieno[3,2-d]pyrimidine or 2-chloro-6-(6-fluoropyridin-3-yl)-4-morpholinothieno[2,3-d]pyrimidine compound, about four equivalents of a primary or secondary amine (R═H, C1-C12 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C12 carbocyclyl, C2-C20 heterocyclyl, C6-C20 aryl, or C1-C20 heteroaryl), and about two eq. diisopropylethylamine in N-methylpyrrolidine (˜0.1M) is heated to about 130-140° C. in a sealed microwave reactor for 10-40 min, followed by removal of volatiles under high vacuum. The crude mixture is purified by flash chromatography to give intermediate 2-chloro-6-(6-aminopyridin-3-yl)-4-morpholinothieno[3,2-d]pyrimidine or 2-chloro-6-(6-aminopyridin-3-yl)-4-morpholinothieno[2,3-d]pyrimidine compound, which may be Suzuki coupled with a fused bicyclic heterocycle or heteroaryl boronate reagent following General Procedure A.

후처리

  1. customfollowed by removal of volatiles under high vacuum
  2. customThe crude mixture is purified by flash chromatography

출처 및 근거

ORD 기록
ord-a843738cb3104daa97e1783e54c1124b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450315B2

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