Hydrochloric Acid → HCID 66955415, compound

HRID 2088450Notes

Reaction equation

HRID 2088450 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:21][C:22]([C:24]1[CH:25]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)[N:26]([CH3:36])[C:27](=[O:35])[N:28](COCCC)[CH:29]=1)=[O:23])[CH3:20].Cl>>[CH2:19]([O:21][C:22]([C:24]1[CH:25]([C:37]2[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=2)[N:26]([CH3:36])[C:27](=[O:35])[NH:28][CH:29]=1)=[O:23])[CH3:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 66955034HCID 66955034, compound

Product 1

HCID 66955415HCID 66955415, compoundYield 97.2%

Conditions

Temperature
65 °C

Procedure

Tetrabutylammonium fluoride (2.1 mL of 1M solution in THF, 2.1 mmol) was added to 4-(4-fluoro-phenyl)-3-methyl-2-oxo-1-propoxymethyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (140 mg, 0.34 mmol) under Ar. The mixture was heated at 65° C. overnight, then cooled. HCl (2N aqueous solution) was added and the mixture was extracted with diethyl ether. The combined extracts were washed with water and brine, dried on Na2SO4, filtered, and concentrated to dryness under reduced pressure. Purification by flash column (hexane/ethyl acetate gradient) gave 4-(4-fluoro-phenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (92 mg, 97%).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe combined extracts were washed with water and brine
  4. customdried on Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by flash column (hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-cc6328bf637e4d3abd1b8b3f997688d0
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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