m-Toluidine → 4-N-(3-methylphenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 2256192Notes

Reaction equation

HRID 2256192 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.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280734-N-(3-methylphenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 67%

Conditions

Temperature
155 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (217 mg, 1.13 mmol) and m-toluidine (1.50 g, 14.0 mmol) is stirred at 155° C. for 30 min. The resulting product is chromatographed over silica gel (5% MeOH/CH2Cl2) to give 7-amino-4-(3-methylanilino)pyrido[4,3-d]pyrimidine (190 mg, 67%) as a pale yellow solid. 1H NMR (DMSO) δ 9.81 (1H, brs), 9.34 (1H, s), 8.38 (1H, s), 7.60 (2H, s), 7.26 (1H, dd, J=8.5, 7.6 Hz), 6.95 (1H, d, J=7.4 Hz), 6.63 (2H, brs), 6.44 (1H, s), 2.33 (3H, s).

Workup

  1. customThe resulting product is chromatographed over silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c43c2c7cf4a743e7a19ac7815a1feefe
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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