Acetic Anhydride → N-{4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidin-7-yl}acetamide

HRID 50802노트

반응식

HRID 50802 반응식
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].C(N(CC)CC)C>CN(C1C=CN=CC=1)C>[C:20]([NH:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1)(=[O:22])[CH3:21]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 3820597-Amino-4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidine

생성물 1

HCID 5328250N-{4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidin-7-yl}acetamide수율 7.7%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

A mixture of 7-amino-4-(3-bromoanilino)-pyrido[4,3-d]pyrimidine (0.154 g, 0.49 mmol), acetic anhydride (0.14 mL, 1.5 mmol), triethylamine (0.14 mL, 1.0 mmol) and a catalytic amount of 4-(N,N-dimethyl-amino)pyridine are stirred under N2 at room temperature for 18 h. The reaction is then quenched by addition of ice water. The dark precipitate is collected by Buchner filtration and is purified by preparative tlc (Rf=0.25, 7% MeOH/CHCl3). Recrystallization from EtOH gives 7-acetylamino-4-(3-bromoanilino)pyrido[4,3-d]-pyrimidine (13.5 mg, 7.7%). 1H NMR (DMSO) δ 10.92 (1H, s), 10.22 (1H, s), 9.64, (1H, s), 8.70 (1H, s), 8.28 (1H, s), 8.21 (1H, s), 7.88 (1H, d, J=7.7Hz) 7.41-7.34 (3H, m), 2.16 (3H, s).

후처리

  1. customThe reaction is then quenched by addition of ice water
  2. filtrationThe dark precipitate is collected by Buchner filtration
  3. customis purified by preparative tlc (Rf=0.25, 7% MeOH/CHCl3)
  4. customRecrystallization from EtOH

출처 및 근거

ORD 기록
ord-70086ee13ce24f689982bb5b90c7cdfb
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713484B2

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