Methanol → 4-Chloro-6-methoxypyrimidine

HRID 358584Notes

Reaction equation

HRID 358584 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[Na].ClCCl.[CH3:13][OH:14]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:14][CH3:13])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 709434,6-DichloropyrimidineHCID 5360545Sodium

Product 1

HCID 10515094-Chloro-6-methoxypyrimidine

Conditions

Temperature
-10 °C

Procedure

3 g of 4,6-dichloropyrimidine were dissolved in 30 ml of dried methanol and mixed dropwise at -10° C. with a solution of 0.46 g of sodium in 20 ml of dried methanol and stirred at -10° C. for 5 hours and at room temperature for 12 hours. The solution was rotated in, the residue taken up with 50 ml of dichloromethane and a little activated carbon was added. After filtration, rotation in to dryness took place. The initially liquid residue became crystalline solid when left to stand. 2.5 g of 4-chloro-6-methoxypyrimidine were obtained.

Workup

  1. additiona little activated carbon was added
  2. filtrationAfter filtration, rotation in to dryness
  3. waitleft

Sources & evidence

ORD record
ord-ca655a4ae9f049d2b3c28fbf04736eea
Source dataset
uspto-grants-1991_03
Patent number
US04997835

Reaction notes

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