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

HRID 361445Notes

Reaction equation

HRID 361445 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, 3 H), 5.25 (s, 2 H), 7.72 (s, 1 H); 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-4304a18f3d274446a86bee16984c83c6
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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