HCID 5328076, compound → HCID 5328065, compound

HRID 2256125Notes

Reaction equation

HRID 2256125 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19]C(=O)C)=[CH:15][CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1>[OH-].[Na+].CO>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 5328076HCID 5328076, compound

Product 1

HCID 5328065HCID 5328065, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 7-amino-4-(4-acetamidoanilino)pyrido[4,3-d]pyrimidine (0.30 g, 1.02 mmole) in aqueous NaOH (2M, 10 mL) and MeOH (10 mL) is stirred at 100° C. for 7 h. The resulting product is chromatographed over alumina (3-4% EtOH/CHCl3) to give 7-amino-4-(4-aminoanilino)pyrido[4,3-d]pyrimidine (86 mg, 33%) as an orange solid. 1H NMR (DMSO) δ 9.58 (1H, brs), 9.24 (1H, s), 8.25 (1H, s), 7.31 (2H d, J=8.6 Hz), 6.58 (2H, d, J=8.6 Hz), 6.48 (2H, brs), 6.39 (1H, s), 5.00 (2H, brs).

Workup

  1. customThe resulting product is chromatographed over alumina (3-4% EtOH/CHCl3)

Sources & evidence

ORD record
ord-2c2f4aacb6494fef90b2465f3a0a4eee
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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