5-Amino-2,4-dichloropyrimidine → 2-Chloro-4-methoxypyrimidin-5-amine

HRID 1384229Notes

Reaction equation

HRID 1384229 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][O-:11].[Na+]>CO>[NH2:1][C:2]1[C:3]([O:11][CH3:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2577975-Amino-2,4-dichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 211863562-Chloro-4-methoxypyrimidin-5-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-2,4-dichloropyrimidine (0.32 g) (obtained as described in Chem. Pharm. Bull., (JAPAN), 1958, 6, 343-346) and a solution of sodium methoxide in methanol (from sodium (0.05 g) and methanol (25 ml)) was heated at reflux for 15 minutes and allowed to cool. Volatile material was removed by evaporation and a small volume of water added. The mixture was extracted twice with ether and the combined extracts were dried (MgSO4) and evaporated to give 5-amino-2-chloro-4-methoxypyrimidine (0.2 g) as an oil; 1H NMR (d6-DMSO): 3.92 (s, 3H), 5.25 (s, 2H), 7.72 (s, 1H); mass spectrum (+ve CI): 160 (M+H)+.

Workup

  1. temperatureat reflux for 15 minutes
  2. temperatureto cool
  3. customVolatile material was removed by evaporation
  4. additiona small volume of water added
  5. extractionThe mixture was extracted twice with ether
  6. dry with materialthe combined extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-bd95a96342704c62b627a828c347bb51
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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