Phosphoric Acid → N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide

HRID 1417004Notes

Reaction equation

HRID 1417004 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([N:9]=[CH:10]N(C)C)=[C:4]([Cl:14])[N:3]=1.P(=O)(O)(O)[OH:16]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH:10]=[O:16])=[C:4]([Cl:14])[N:3]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 11107249N'-(2-Amino-4,6-dichloro-5-pyrimidinyl)-N,N-dimethylmethanimidamide

Product 1

HCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamideYield 72%

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

In another experiment, a slurry of 2-amino-4,6-dichloro-5-{[(dimethylamino)methylene]-amino}-pyrimidine (Example 2, 25.0 g, 0.107 mol) in 1.5 M aqueous potassium phosphate buffer (300 mL, prepared as above) was gently refluxed for 4 hours. pH was maintained at 3.2 by addition of 85% phosphoric acid, as required, throughout this period. The precipitate was filtered, washed with water (3×10 mL), methanol (2×10 mL), and dried (50° C., 25 mm Hg) to give the title compound as an off-white powder (16.0 g, 72%) with purity identical to that of the characterized sample described above (elemental analysis and 1H-NMR).

Workup

  1. waitas required, throughout this period
  2. filtrationThe precipitate was filtered
  3. washwashed with water (3×10 mL), methanol (2×10 mL)
  4. customdried (50° C., 25 mm Hg)

Sources & evidence

ORD record
ord-c0c64bdb74214c7fad654eaf7d7b0167
Source dataset
uspto-grants-1999_06
Patent number
US05917041

Reaction notes

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