Water → HCID 14347505, compound

HRID 1199478Notes

Reaction equation

HRID 1199478 reaction equation
[H-].[Na+].[CH:3]1([C:9]2[NH:10][C:11](=[O:19])[C:12]([C:17]#[N:18])=[C:13]([S:15][CH3:16])[N:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].O>COCCOC>[C:17]([C:12]1[C:11](=[O:19])[N:10]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:9]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)=[N:14][C:13]=1[S:15][CH3:16])#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 14347504HCID 14347504, compound

Product 1

HCID 14347505HCID 14347505, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred suspension of NaH (50% dispersion in mineral oil, washed with hexane, 2.2 g, 0.047 mol) in DME (350 mL) was added 2-cyclohexyl-1,6-dihydro-4-(methylthio)-6-oxo-5-pyrimidinecarbonitrile (9.5 g, 0.038 mol) in several portions. After 1 hour, methyl bromoacetate was added and the resulting solution was heated at 95°-100° C. for 2 days. The solution was cooled and water (300 mL) was added. The mixture was extracted with ethyl acetate and the combined extracts were washed with water, dried (MgSO4), and concentrated to give a beige powder (12.2 g, 99%) which was used without further purification.

Workup

  1. temperaturethe resulting solution was heated at 95°-100° C. for 2 days
  2. temperatureThe solution was cooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aaf9b468517049a4b83d87f5bea4df66
Source dataset
uspto-grants-1990_02
Patent number
US04900829

Reaction notes

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