Sodium hydride → HCID 20490675, compound

HRID 435064Notes

Reaction equation

HRID 435064 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:6]([OH:7])[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1.[H-].[Na+].[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1Cl>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH3:19][C:2]1([CH3:1])[CH:6]([O:7][C:23]2[N:24]=[CH:25][CH:26]=[CH:27][N:22]=2)[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 20490686HCID 20490686, compound

Product 1

HCID 20490675HCID 20490675, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

1 g of the alcohol of Example 3 was added to 220 mg of a 50% suspension of sodium hydride in oil dissolved in toluene (15 ml) and the mixture was stirred under reflux for 1 hour. 2-pyrimidinyl chloride (625 mg) in 10 ml toluene was added over 30 minutes. The mixture was stirred at reflux temperature for 16 hours. The mixture was then poured into brine and extracted with diethyl ether. The ether extract was dried over magnesium sulphate and evaporated to yield a residue which was purified on a silica gel column using 8% acetone in petrol as eluant to give 1.25 g (97%) of the desired product.

Workup

  1. temperatureunder reflux for 1 hour
  2. stirringThe mixture was stirred
  3. temperatureat reflux temperature for 16 hours
  4. extractionextracted with diethyl ether
  5. extractionThe ether extract
  6. dry with materialwas dried over magnesium sulphate
  7. customevaporated
  8. customto yield a residue which
  9. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-9cace9cb7e434438ae8d22cee530f745
Source dataset
uspto-grants-1983_08
Patent number
US04400198

Reaction notes

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