Hydrochloric Acid → 2-Amino-2-(pyrimidin-5-yl)acetamide

HRID 1681901Notes

Reaction equation

HRID 1681901 reaction equation
[NH2:1][CH:2]([C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1)[C:3]#[N:4].Cl.C(=O)([O-])[O-:13].[Na+].[Na+]>>[NH2:1][CH:2]([C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1)[C:3]([NH2:4])=[O:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 20080448alpha-Amino-5-pyrimidineacetonitrile

Product 1

HCID 200804132-Amino-2-(pyrimidin-5-yl)acetamideYield 81%

Procedure

Amino(pyrimidin-5-yl)acetonitrile (1.1 g, 8.2 mmol) is hydrolyzed by refluxing in a small volume of dilute HCl for 1 hour. The pH is raised to 10 by addition of saturated sodium carbonate and the mixture then extracted with chloroform. Evaporation of the chloroform and chromatography (silica, chloroform/methanol) gives product as a yellow solid 950 mg (81%) ms m/z=142.

Workup

  1. extractionthe mixture then extracted with chloroform
  2. customEvaporation of the chloroform and chromatography (silica, chloroform/methanol)

Sources & evidence

ORD record
ord-9d404f5546614c35a0c8b8e4181c91fd
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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