HCID 20491763, compound → HCID 20491781, compound

HRID 434658Notes

Reaction equation

HRID 434658 reaction equation
Br[CH2:2][CH:3]([OH:13])[CH2:4][N:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[N:7][C:6]1=[O:12]>O1CCCC1>[Cl:11][C:9]1[CH:8]=[N:7][C:6](=[O:12])[N:5]([CH2:4][CH:3]2[O:13][CH2:2]2)[CH:10]=1

Participants

3

Reactant 1

HCID 20491763HCID 20491763, compound

Product 1

HCID 20491781HCID 20491781, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous M-sodium hydroxide solution (2.5 ml) was added to a stirred solution of 1-(3-bromo-2-hydroxypropyl)-5-chloropyrimidin-2-one (669 mg) in tetrahydrofuran (50 ml) and the mixture was stirred at room temperature. After 1 h the reaction mixture was evaporated to a yellow solid which was subjected to column chromatography on silica developing and eluting with chloroform-ethanol, 19:1. This gave a white crystalline solid which was recrystallised from ethyl acetate to give white crystals of the title pyrimidinone (59 mg), m.p. 132°-135° C., λmax (EtOH) 227 nm (E11 522), 332.5 nm (E11 160).

Workup

  1. customAfter 1 h the reaction mixture was evaporated to a yellow solid which
  2. washeluting with chloroform-ethanol, 19:1
  3. customThis gave a white crystalline solid which
  4. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-3ff0f130859d4d67bf8b8d87335b07d0
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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