Acrylonitrile → 5-(4-Methoxyphenyl)-6-phenyl-N-{3-[2-cyanoethoxy]propyl}furo[2,3-d]pyrimidine-4-amine

HRID 1926879노트

반응식

HRID 1926879 반응식
[C:1](#[N:4])[CH:2]=[CH2:3].CC[O-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])=[N:23][CH:22]=[N:21][C:20]=3[O:19][C:18]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:13][CH:12]=1>CS(C)=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:25]3[C:24]([NH:26][CH2:27][CH2:28][CH2:29][O:30][CH2:3][CH2:2][C:1]#[N:4])=[N:23][CH:22]=[N:21][C:20]=3[O:19][C:18]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 7855AcrylonitrileHCID 2723922Sodium ethoxideHCID 580168233-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol

생성물 1

HCID 580168795-(4-Methoxyphenyl)-6-phenyl-N-{3-[2-cyanoethoxy]propyl}furo[2,3-d]pyrimidine-4-amine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

Add 47 mg (0.89 mmol) acrylonitrile and 57 mg (0.83 mmol) sodium ethylate to 300 mg (0.80 mmol) of the compound from Stage 1. Stir the mixture overnight at 80° C. After cooling, take up the mixture in DMSO and purify directly by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). 160 mg (47% of theor.) of the title compound is obtained as a yellow oil.

후처리

  1. temperatureAfter cooling
  2. custompurify directly by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)

출처 및 근거

ORD 기록
ord-8ed139b7c6bc4bf797d30a72ed8a48b3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183246B2

반응 노트

불러오는 중…