Formamide → 6-Amino-5-nitroso-2-pyridin-3-ylpyrimidin-4-ylamine

HRID 2164328

Reaction equation

HRID 2164328 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=C[NH:13]3)=[C:9]([NH2:16])[N:8]=2)[CH:2]=1.C(N)(=N)C1C=CC=NC=1.C(N)=[O:27]>>[NH2:16][C:9]1[C:10]([N:11]=[O:27])=[C:14]([NH2:13])[N:15]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 2020433-PyridinecarboxamidineHCID 178508302HCID 178508302, compound

Product 1

HCID 2309336-Amino-5-nitroso-2-pyridin-3-ylpyrimidin-4-ylamine

Procedure

Taylor et al [J. Am. Chem. Soc. 81, 2442-8 (1959)] show, inter alia, the preparation of 2-(3-pyridinyl)-9H-purin-6-amine by heating the nicotinamidine salt of isonitrosomalonitrile in formamide to produce 4,6-diamino-5-nitroso-2-(3-pyridinyl)pyrimidine and heating the reaction mixture containing said 5-nitroso compound and formamide with a mixture of formic acid and sodium dithionite dihydrate to produce said 2-(3-pyridinyl)-9H-purin-6-amine, for which no use is indicated.

Sources & evidence

ORD record
ord-1b7c567ef25b46b89b1e923bbc04eaef
Source dataset
uspto-grants-1985_03
Patent number
US04503228

Linked notes

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