Sodium hydride → 2-(2-isopropyl-1H-imidazol-1-yl)-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidine

HRID 881311

반응식

HRID 881311 반응식
[CH:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([CH3:3])[CH3:2].[H-].[Na+].Cl[C:12]1[N:13]=[C:14]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[C:15]2[S:20][C:19]([CH2:21][N:22]3[CH2:27][CH2:26][N:25](S(C)(=O)=O)[CH2:24][CH2:23]3)=[CH:18][C:16]=2[N:17]=1>CN(C)C=O.C(OCC)(=O)C>[CH:1]([C:4]1[N:5]([C:12]2[N:13]=[C:14]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)[C:15]3[S:20][C:19]([CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:18][C:16]=3[N:17]=2)[CH:6]=[CH:7][N:8]=1)([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 236508374-(2-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

생성물 1

HCID 669341512-(2-isopropyl-1H-imidazol-1-yl)-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

To 2-isopropylimidazole (28 mg) in dry N,N-dimethylformamide (1 ml) was added sodium hydride (10 mg, 60% dispersion in mineral oil). After 30 minutes, 2-chloro-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, was added and the reaction mixture was heated in the microwave for 45 minutes at 120° C. The reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo and the residue purified using flash chromatography to yield 176. NMR (400 MHz CDCl3): 1.19 (1H, s, CH), 1.30 (6H, d(J=6.84), 2.61-2.63 (4H, m, CH2), 2.74 (3H, s, CH3), 3.23-3.25 (4H, m, CH2), 3.79-3.82 (6H, m, CH2), 3.92-3.94 (4H, m, CH2), 6.92 (1H, s, ar), 7.18 (1H, s, ar), 7.66 (1H, d(J=1.49), ar). MH+ 506.30

후처리

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customthe residue purified

출처 및 근거

ORD 기록
ord-7baf5e23015d45228f1b86fa164812c7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993563B2

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