Methanol → HCID 20213160, compound

HRID 1905843Notes

Reaction equation

HRID 1905843 reaction equation
[Cl:1][C:2]1[C:7]([O:8]C)=[C:6]([Cl:10])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.B(Cl)(Cl)Cl.CO>C(Cl)Cl>[Cl:10][C:6]1[C:7]([OH:8])=[C:2]([Cl:1])[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 20213162HCID 20213162, compound

Product 1

HCID 20213160HCID 20213160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

15.3 g of 4,6-dichloro-5-methoxy-2-phenylpyrimidine and 30 ml of 25% boron trichloride solution in methylene chloride are heated at 40° C. in a bomb tube for 15 hours. The reaction mixture is subsequently added dropwise to a mixture of methanol and methylene chloride (1:1), and then diluted with ice-water. The organic phase is separated, and the aqueous phase is extracted with methylene chloride. The combined organic phases are concentrated by evaporation and chromatographed on silica gel to thus obtain 8.7 g of 4,6-dichloro-5-hydroxy-2-phenylpyrimidine, m.p. 138°-140° C. (compound No. 34).

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is extracted with methylene chloride
  3. concentrationThe combined organic phases are concentrated by evaporation
  4. customchromatographed on silica gel to thus obtain 8.7 g of 4,6-dichloro-5-hydroxy-2-phenylpyrimidine, m.p. 138°-140° C. (compound No. 34)

Sources & evidence

ORD record
ord-59d0455b5e0944d8bca4e5729cdb9ff6
Source dataset
uspto-grants-1987_03
Patent number
US04648896

Reaction notes

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