Methanol → 2,4-Dichloro-6-methoxypyrimidine

HRID 326487Notes

Reaction equation

HRID 326487 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.CO.N1C(C)=CC(C)=CC=1C.C[CH2:22][O:23]CC>O1CCCC1>[CH3:22][O:23][C:6]1[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:9])[CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 79532,4,6-TrimethylpyridineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 38245092,4-Dichloro-6-methoxypyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4,6-trichloropyrimidine (55 g), methanol (50 ml) and collidine (50 g) is heated in dry tetrahydrofuran (400 ml) for 48 hr. Ether is added and the precipitate is collected. The precipitate is column chromatographed on silica gel to give 6-methoxy-2,4-dichloropyrimidine. This product is mixed with morpholine in THF and stirred at 20°-25° to give 6-methoxy-2-morpholino-4-chloropyrimidine. The 6-methoxy-2-morpholino-4-chloropyrimidine is heated with piperazine in pyridine at 60° for 24 hr to give the title compound.

Workup

  1. customthe precipitate is collected
  2. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2533294eb3fd4efdaadae161edeacc11
Source dataset
uspto-grants-1993_12
Patent number
US05268477

Reaction notes

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