Water → 2,5-Diamino-4,6-dichloropyrimidine

HRID 1267586Notes

Reaction equation

HRID 1267586 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9]C=O)=[C:4]([Cl:12])[N:3]=1.O.P(=O)(O)(O)O>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH2:9])=[C:4]([Cl:12])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide

Product 1

HCID 3010392,5-Diamino-4,6-dichloropyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4,6-dichloro-5-[(dimethylamino)methylene]amino}pyrimidine (Example 2, 500 mg, 2.14 mmol), pH 3.2 aqueous potassium phosphate buffer (1.5 M, 6 mL, prepared as described in Example 3), water (1 mL), and ethanol (5 mL) was refluxed gently for 28 hours. During the reflux period, pH was maintained at ca. 3 by addition of 85% phosphoric acid. Volatiles were evaporated in vacuo and the residual solids partitioned between water (30 mL, adjusted to pH 8 with dilute ammonium hydroxide) and chloroform (75 mL. The chloroform layer was dried (sodium sulfate) and the chloroform evaporated to leave off-white solid (0.30 g). Crystallization of this solid from ethanol:water/4:1 gave the title compound (IV) as light pink needles (332 mg, 61%); darkens and shrinks to black solid above 185° C., does not become fluid below 300° C.; 1H-NMR (DMSO-d6) and mass spectra identical to those described in Example 4.

Workup

  1. temperaturewas refluxed gently for 28 hours
  2. customVolatiles were evaporated in vacuo
  3. customthe residual solids partitioned between water (30 mL, adjusted to pH 8 with dilute ammonium hydroxide) and chloroform (75 mL
  4. dry with materialThe chloroform layer was dried (sodium sulfate)
  5. customthe chloroform evaporated

Sources & evidence

ORD record
ord-24c583412e974ccd965d175e0dd4809c
Source dataset
uspto-grants-2003_04
Patent number
US06552193B1

Reaction notes

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