Triethylamine → 2-{2-[(1-Aminocyclohexyl)ethynyl]-1-methyl-4-phenyl-1H-imidazol-5-yl}[1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 32612노트

반응식

HRID 32612 반응식
Br[C:2]1[N:3]([CH3:23])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[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(N(CC)CC)C.[C:31]([C:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)#[CH:32]>[Cu]I.CN(C=O)C>[NH2:39][C:33]1([C:31]#[C:32][C:2]2[N:3]([CH3:23])[C:4]([C:13]3[S:14][C:15]4[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[C:20]=4[N:21]=3)=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1216911-EthynylcyclohexylamineHCID 100687782-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

생성물 1

HCID 100941732-{2-[(1-Aminocyclohexyl)ethynyl]-1-methyl-4-phenyl-1H-imidazol-5-yl}[1,3]thiazolo[5,4-d]pyrimidin-7-amine수율 41%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 2-(2-bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 26) (0.02 g), PdCl2dppf (3.5 mg), triethylamine (0.1 mL), DMF (5 mL), copper(I) iodide (1 mg) and 1-ethynylcyclohexylamine (0.034 mL) was heated at 90° C., under an inert atmosphere, for 1.5 hours. The solvent was evaporated in vacuo then purification by flash chromatography on silica eluting with DCM:MeOH (9:1) gave the title compound as a beige solid (9 mg, 41%).

후처리

  1. customThe solvent was evaporated in vacuo
  2. custompurification by flash chromatography on silica eluting with DCM:MeOH (9:1)

출처 및 근거

ORD 기록
ord-a81e4381c68245269f89f1a2f7f08e98
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427616B2

반응 노트

불러오는 중…