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

HRID 1386176Notes

Reaction equation

HRID 1386176 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

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-dimethylamino)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).

Workup

  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

Sources & evidence

ORD record
ord-03790fe1fed848be861b524478c64f3b
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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