Formic Acid → N-(4,6-dichloro-2-formamido-pyrimidin-5-yl)formamide

HRID 1089246Notes

Reaction equation

HRID 1089246 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[NH2:8][C:9]1[N:14]=[C:13]([Cl:15])[C:12]([NH2:16])=[C:11]([Cl:17])[N:10]=1.[CH:18](O)=[O:19]>>[Cl:17][C:11]1[C:12]([NH:16][CH:18]=[O:19])=[C:13]([Cl:15])[N:14]=[C:9]([NH:8][CH:5]=[O:7])[N:10]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 3010392,5-Diamino-4,6-dichloropyrimidine

Product 1

HCID 13989892N-(4,6-dichloro-2-formamido-pyrimidin-5-yl)formamideYield 60%

Conditions

Temperature
20 °C

Procedure

Acetic anhydride (40 ml) was added dropwise over 10 minutes to a mixture of 2,5-diamino-4,6-dichloropyrimidine (8.0 g, 44.7 mmol) and formic acid (100 ml) at 0° C. The mixture was stirred at 20° C. for 4 hours, evaporated to dryness and co-evaporated with toluene. Solidification from acetone-hexane afforded the title compound (6.1 g, 60%). IR: υmax (KBr) 3230, 1715, 1680, 1575, 1550, 1485, 1415 cm-1. Found m/e 233.9695; C6H4N4O2Cl2 requires 233.9709.

Workup

  1. customevaporated to dryness and co-evaporated with toluene

Sources & evidence

ORD record
ord-e462c844d81c4a4bad308da2a54bbdab
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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