Hydrochloric Acid → 4-N-(2-nitrophenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 1386162

Reaction equation

HRID 1386162 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.[N+:14]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19])([O-:16])=[O:15].Cl.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N+:14]([O-:16])=[O:15])=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 516892Sodium BicarbonateHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280524-N-(2-nitrophenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 33.3%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (220 mg, 1.15 mmole) and 2-nitroaniline (2.00 g, 14.5 mmole) is heated to 100° C., then excess dry HCl gas is added to the hot stirred solution, and the mixture stirred at 160° C. for 20 min. The resulting product is neutralized with excess NaHCO3, dissolved in MeOH/CHCl3, dried onto silica gel and chromatographed over silica gel (2-4% MeOH/CH2Cl2) to give 7-amino-4-(2-nitroanilino)pyrido[4,3-d]pyrimidine (108 mg, 33%) as a yellow brown solid. 1H NMR (DMSO) δ 10.40 (1H, brs), 9.24 (1H, brs), 8.20 (1H, brs), 8.12 (1H, brs), 8.01 (2H, brs), 7.75 (1H, brs), 6.70 (2H, brs), 6.43 (1H, brs)

Workup

  1. customdried onto silica gel
  2. customchromatographed over silica gel (2-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cabb8da88a674fb09a52eb0d32fe963c
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Linked notes

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