3-Furanmethanol → HCID 20491772, compound

HRID 434652Notes

Reaction equation

HRID 434652 reaction equation
C(O[CH:7]([O:11][CH2:12][C:13]([CH3:16])([CH3:15])C)N(C)C)C(C)(C)C.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.O1C=CC(CO)=C1>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:16][C:13]2[CH:15]=[CH:7][O:11][CH:12]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 204493-FuranmethanolHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 20491772HCID 20491772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred mixture of 5-chloropyrimidin-2-one (522 mg) and 3-furanmethanol (0.48 ml) in dry N,N-dimethylformamide (10 ml) under nitrogen and the mixture was then heated at 90° C. After 11/4 h the reaction mixture was evaporated to dryness and then the residue was dissolved in ethyl acetate (200 ml) and the solution washed with water (3×50 ml), dried (MgSO4) and concentrated to ca 15 ml by which time crystallisation had occurred. The suspension was cooled and then the crystals collected and recrystallised from ethyl acetate to give white crystals of the title pyrimidinone (288 mg), m.p. 161.5°-162° C., λmax (EtOH) 333 nm (ε 2,340), λinf 245 nm (ε 4,000).

Workup

  1. customAfter 11/4 h the reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in ethyl acetate (200 ml)
  3. washthe solution washed with water (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to ca 15 ml by which time crystallisation
  6. temperatureThe suspension was cooled
  7. customthe crystals collected
  8. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-dfa4c6a0893c48a2b15670ba790fa321
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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