N,N-dimethyl-p-phenylenediamine → Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[4-(dimethylamino)phenyl]-

HRID 1386161Notes

Reaction equation

HRID 1386161 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:14][N:15]([CH3:23])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:22][C:19]3[CH:20]=[CH:21][C:16]([N:15]([CH3:23])[CH3:14])=[CH:17][CH:18]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328068Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[4-(dimethylamino)phenyl]-Yield 53.1%

Conditions

Temperature
190 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (256 mg, 1.33 mmole) and N,N-dimethyl-1,4-phenylenediamine (1.95 g, 14.4 mmole) is stirred under N2 at 190° C. for 20 min. The resulting product is chromatographed over alumina (3-7% EtOH/CHCl3) to give 7-amino-4-(4-dimethylaminoanilino)pyrido[4,3-d]pyrimidine (198 mg, 53%) as an orange solid. 1H NMR (DMSO) δ 9.67 (1H, brs), 9.27 (1H, s), 8.27 (1H, s), 7.51 (2H, d, J=8.9 Hz), 6.75 (2H, d, J=8.9 Hz), 6.51 (2H, brs), 6.39 (1H, s), 2.89 (6H, s).

Workup

  1. customThe resulting product is chromatographed over alumina (3-7% EtOH/CHCl3)

Sources & evidence

ORD record
ord-e8209ea1428f48ff9352bfbf5057e866
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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