3,4-Dichloroaniline → HCID 22736823, compound

HRID 2256131Notes

Reaction equation

HRID 2256131 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.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH2:18]>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:18][C:17]3[CH:19]=[CH:20][C:21]([Cl:22])=[C:15]([Cl:14])[CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 22736823HCID 22736823, compoundYield 64%

Conditions

Temperature
165 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (247 mg, 1.29 mmol) and 3,4-dichloroaniline (1.50 g, 9.26 mmol) is stirred at 165° C. for 30 min. The resulting product is chromatographed over silica gel (7-8% MeOH/CH2Cl2) to give 7-amino-4-(3,4-dichloroanilino)pyrido[4,3-d]pyrimidine (252 mg, 64%) as a pale yellow solid. 1H NMR (DMSO) δ 9.97 (1H, brs), 9.34 (1H, s), 8.47 (1H, s), 8.29 (1H, brs), 7.86 (1H, brd, J=8.6 Hz), 7.62 (1H, d, J=8.8 Hz), 6.70 (2H, brs), 6.46 (1H, s).

Workup

  1. customThe resulting product is chromatographed over silica gel (7-8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-392cefbc972540f4850d46199da08f74
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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