Sodium Hydroxide → 6-Chloro-2,3-dihydro-3-hydroxy-2-imino-4-pyrimidinamine

HRID 1973664Notes

Reaction equation

HRID 1973664 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[N:3]=1.ClC1C=CC=C(C(OO)=[O:18])C=1.[OH-].[Na+]>>[NH2:8][C:6]1[N:5]([OH:18])[C:4](=[NH:9])[N:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 674322,4-Diamino-6-chloropyrimidineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 15515256-Chloro-2,3-dihydro-3-hydroxy-2-imino-4-pyrimidinamineYield 44.7%

Procedure

A 30 g. (0.15 mole) quantity of 4-chloro-2,6-diaminopyrimidine is dissolved in 600 ml. of hot 3A alcohol, the solution cooled to 0°-10° C. and 41.8 g. (0.24 mole) of m-chloroperbenzoic acid is added. The mixture is held at 0°-10° C. for 4 hours and filtered. The solid is shaken for 2 hours in 0.24 mole of 10% sodium hydroxide and filtered. The solid is washed with water and dried to yield 19.3 g. of crude product. This product is extracted for 1 hour with 900 ml. of boiling acetonitrile to yield 14.8 g. (44.7% yield) of 6-amino-4-chloro-1,2-dihydro-1-hydroxy-2-imino pyrimidine, m.p. 193° C.

Workup

  1. filtrationfiltered
  2. filtrationfiltered
  3. washThe solid is washed with water
  4. customdried
  5. customto yield 19.3 g
  6. extractionThis product is extracted for 1 hour with 900 ml
  7. customof boiling acetonitrile to yield 14.8 g

Sources & evidence

ORD record
ord-e7ffd76dc30b4414ae074aa1ead7e0cb
Source dataset
uspto-grants-1976_12
Patent number
US03998827

Reaction notes

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