Sodium Carbonate → 2-(1-Methyl-2,4-diphenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine

HRID 32545ノート

反応式

HRID 32545 の反応式
Br[C:2]1[N:3]([CH3:24])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([S:22][CH3:23])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COCCOC.O.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][N:3]1[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([S:22][CH3:23])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=[C:2]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 691944812-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine2 回

生成物 1

HCID 691943112-(1-Methyl-2,4-diphenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine収率 52.4%

試薬・触媒・溶媒 3

HCID 178420553HCID 178420553、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-(2-bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)-[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 37) (50 mg), tetrakis(triphenylphosphino)palladium(0) (28 mg), sodium carbonate (33 mg) and phenylboronic acid (14 mg) in DME (2 mL) and water (1 mL) was heated at 90° C. for 2 hours. After cooling to ambient temperature and extraction into DCM (3×5 mL), the combined organics were dried, filtered and the solvent evaporated in vacuo to give a brown oil. Purification by flash chromatography on silica eluting with EtOAC:hexane (1:9) gave the title compound as a yellow solid (25 mg, 50%);

後処理

  1. temperatureAfter cooling to ambient temperature
  2. extractionextraction into DCM (3×5 mL)
  3. customthe combined organics were dried
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto give a brown oil
  7. customPurification by flash chromatography on silica eluting with EtOAC

出典と根拠

ORDレコード
ord-56afae63d6544ed7899836d3083b2e3b
出典データセット
uspto-grants-2008_09
特許番号
US07427616B2

反応ノート

読み込み中…