Dichloromethane → HCID 18932912, compound

HRID 1656503Notes

Reaction equation

HRID 1656503 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]([O:13]CC)=[O:12])=[CH:7][N:6]=[C:5]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]=[CH2:3].[OH-].[Na+].ClCCl>O1CCCC1>[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]([OH:13])=[O:12])=[CH:7][N:6]=[C:5]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 18932921HCID 18932921, compound

Product 1

HCID 18932912HCID 18932912, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-allyl-2-phenylpyrimidin-6(1H)-one-5-carboxylate (25.6 g) in tetrahydrofuran (300 mL) at 0° C. was added a solution of 0.5N sodium hydroxide (198 mL). The resulting solution was allowed to stir for 1 h, was poured into dichloromethane and the organic layer removed. The remaining basic aqueous fraction was extracted with dichloromethane, made acidic with 1N hydrochloric acid (to pH 2), and extracted with dichloromethane. The organic layers from the acidic extractions were dried and evaporated to give an oil which crystallized upon addition of ether. The resulting white solid was collected and washed with ether:hexane (1:1) to give 1-allyl-2-phenylpyrimidin-6(1H)-one-5-carboxylic acid (11.1 g); 300 MHz NMR: 13.0 (s broad,1), 8.69 (s,1), 7.58 (m,5), 5,82 (m,1), 5.16 (d,1), 4.87 (d,1), 4.51 (d,2).

Workup

  1. customthe organic layer removed
  2. extractionThe remaining basic aqueous fraction was extracted with dichloromethane
  3. extractionextracted with dichloromethane
  4. extractionThe organic layers from the acidic extractions
  5. customwere dried
  6. customevaporated
  7. customto give an oil which
  8. customcrystallized upon addition of ether
  9. customThe resulting white solid was collected
  10. washwashed with ether:hexane (1:1)

Sources & evidence

ORD record
ord-8e9711ae1e6a4cf3a3f8006001d8adce
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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