Benzyl Alcohol → 2-Amino-4-benzyloxy-6-furan-2-yl-pyrimidine-5-carbonitrile

HRID 1355734

반응식

HRID 1355734 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4](S(C)(=O)=O)[N:3]=1.[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCN2C(=NCCC2)CC1>C(COC)OC>[NH2:1][C:2]1[N:3]=[C:4]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 185073992-Amino-4-furan-2-yl-6-methanesulfonyl-pyrimidine-5-carbonitrile

생성물 1

HCID 98145812-Amino-4-benzyloxy-6-furan-2-yl-pyrimidine-5-carbonitrile수율 56%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

To a stirred suspension of 300 mg (1.14 mmol) 2-amino-4-furan-2-yl-6-methanesulfonyl-pyrimidine-5-carbonitrile in 9 ml dimethoxyethane were added 0.41 ml (4.0 mmol) benzyl alcohol and 0.25 ml (1.7 mmol) DBU and the mixture heated at 100° C. for 1 hour. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate/hexane 2/1) followed by trituration in ether/hexane afforded 185 mg (56%) 2-amino-4-benzyloxy-6-furan-2-yl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 292 (M+, 40), 91 (C7H7+, 100).

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo

출처 및 근거

ORD 기록
ord-43fd914ddf3e4ff29c59ab53cf3367e3
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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