Benzamidine → 6-Oxo-4-(4-phenoxyphenyl)-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile

HRID 81041

반응식

HRID 81041 반응식
[C:1](/[C:3](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)/[C:4]([O:6]CC)=O)#[N:2].[C:23]([NH2:31])(=[NH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>CO>[O:6]=[C:4]1[NH:31][C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:30][C:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)=[C:3]1[C:1]#[N:2]

참가 물질

5

반응물 3

HCID 2332BenzamidineHCID 8857Ethyl AcetateHCID 86665688(E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

생성물 1

HCID 1363723496-Oxo-4-(4-phenoxyphenyl)-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate (100 mg, 0.341 mmol) and benzamidine (45.1 mg, 0.375 mmol) in methanol (1 mL) was stirred at room temperature for 15 h while opening to the air. The mixture was treated with ethyl acetate (30 mL), washed with water (5 mL), brine (5 mL), dried (MgSO4) and concentrated to give crude 6-oxo-4-(4-phenoxyphenyl)-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile as tan solid. The crude material was taken to next reaction without purification. MS (ES+) m/z: 366 (M+H); LC retention time: 4.525 min (analytical HPLC Method B).

후처리

  1. washwashed with water (5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9b38a98df425408583cd019796b1d46e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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