Sodium Hydroxide → HCID 18326593, compound

HRID 1250705Notes

Reaction equation

HRID 1250705 reaction equation
C[O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[N:7]([CH3:13])[C:8](=[O:12])[NH:9][C:10]=1[CH3:11])=[O:4].[OH-].[Na+]>CO>[F:21][C:16]1[CH:15]=[C:14]([CH:6]2[C:5]([C:3]([OH:4])=[O:2])=[C:10]([CH3:11])[NH:9][C:8](=[O:12])[N:7]2[CH3:13])[CH:19]=[CH:18][C:17]=1[F:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20718797HCID 20718797, compound

Product 1

HCID 18326593HCID 18326593, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
500 °C

Procedure

(−)-4-(3,4-Difluorophenyl)-3,6-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester (650 mg, 2.19 mmol) was dissolved in methanol (10 ml), treated with 2.5N sodium hydroxide (10 ml), and warmed to 500° C. for 8hr. The solvent was removed in vacuo, the remaining aqueous phase treated with 10% KHSO4 (aq), and extracted with ethyl acetate (3X). The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated to dryness in vacuo to give a crude oil. Crystallization from diethyl ether gave the product as a white solid [αD]=−128°, c=0.20 MeOH).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe remaining aqueous phase treated with 10% KHSO4 (aq)
  3. extractionextracted with ethyl acetate (3X)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo
  8. customto give a crude oil
  9. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-efe52d08990148af8201c6b401dc19ea
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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