Dimethylamine → HCID 22112887, compound

HRID 564769Notes

Reaction equation

HRID 564769 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:16]1[C:17]2[CH:25]=[C:24]([Cl:26])[N:23]=[CH:22][C:18]=2[N:19]=[CH:20][N:21]=1.C(N(CC)CC)C.CNC>CC(O)C>[Cl:26][C:24]1[N:23]=[CH:22][C:18]2[N:19]=[CH:20][N:21]=[C:16]([NH:12][C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:14][CH:13]=3)[C:17]=2[CH:25]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 8764(4-Aminophenoxy)benzeneHCID 108218764,6-Dichloropyrido[3,4-d]pyrimidine

Product 1

HCID 22112887HCID 22112887, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6-Chloro-4-(4-phenoxyanilino)pyrido[3,4-d]pyrimidine was prepared by the reaction of 4-phenoxyaniline and 4,6-dichloropyrido[3,4-d]pyrimidine in 2-propanol according to Procedure A, with triethylamine present to give the free base of the product directly. Reaction of this product with dimethylamine (33% aqueous solution) according to Procedure C gave the title compound: δH (CDCl3) 9.00 (1H,s), 8.54 (1H,s), 7.70 (2H, d), 7.00-7.44 (5H,m), 7.13 (2H,d), 6.38 (1H,s), 3.22 (6H,s); m/z (M+1)+358.

Workup

  1. customto give the free base of the product directly

Sources & evidence

ORD record
ord-be3170958658475aa18e259a95abb570
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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