Formic Acid → N-(5-amino-4,6-dichloropyrimidin-2-yl)-formamide

HRID 2084581Notes

Reaction equation

HRID 2084581 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH2:9])=[C:4]([Cl:10])[N:3]=1.[CH:11](O)=[O:12].C1(C)C=CC=CC=1.O>>[NH2:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([NH:1][CH:11]=[O:12])=[N:7][C:6]=1[Cl:8]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 1140TolueneHCID 3010392,5-Diamino-4,6-dichloropyrimidine

Product 1

HCID 10219921N-(5-amino-4,6-dichloropyrimidin-2-yl)-formamideYield 1,000%

Conditions

Temperature
2.5 °C

Procedure

A solution of 2,5-diamino-4,6-dichloro-pyrimidine (0.001 mol; 2.0 g) and 98% strength formic acid (0.5 mol, 22.96 g, 18.8 ml) was stirred overnight at room temperature. Toluene (0.94 mol, 86.76 g, 18.82 ml) was then added and the reaction was cooled to 0-5° C. The product was filtered off and washed with water (1.11 mol, 20.0 g, 20.0 ml). The product was subsequently dried at 50° C. in vacuo. N-(5-Amino-4,6-dichloropyrimidin-2-yl)formamide was detected in the 1H NMR as a single product. 0.01 mol (1.62 g) of the abovementioned product was obtained, corresponding to a yield of about 70%.

Workup

  1. filtrationThe product was filtered off
  2. customThe product was subsequently dried at 50° C. in vacuo

Sources & evidence

ORD record
ord-14a0a31cd191415caae8c22b9d087b40
Source dataset
uspto-grants-2004_04
Patent number
US06716981B2

Reaction notes

Loading…