Sodium hydride → 2-Methylpyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate

HRID 1074151Notes

Reaction equation

HRID 1074151 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH:11]1([C:17]2([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CC(N(C)C)=O>[CH:11]1([C:17]2([C:23]([O:8][C:5]3[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=3)=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5358572-Methylpyrimidin-5-olHCID 221559231-Cyclohexylcyclohexane-1-carbonyl chloride

Product 1

HCID 221558802-Methylpyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

To an ice-cooled mixture of 2-methyl-5hydroxypyrimidine (0.9 g) and sodium hydride 80% (0.24 g) in dimethylacetamide (15 ml), a solution of 1-cyclohexylcyclohexane-1-carbonyl chloride (1.68 g) in dimethylacetamide (10 ml) was added. The mixture was then stirred at room temperature for 1 hour, then filtered and evaporated in vacuo. The residue was taken up with ethyl acetate, which was washed with water and dried. Evaporation of the solvent and column chromatography (cyclohexane/ethyl acetate 9:1) afforded 1.2 g of 2-methylpyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate. M.p. 52°-55° C. According to the procedure above described the following compound was also prepared, 2-methylpyrimidin-5-yl α-cyclopentylphenyl glicolate hydrochloride. M.p. 132°-138° C.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. washwas washed with water
  4. customdried
  5. customEvaporation of the solvent and column chromatography (cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-8f2b5e34323e4b73be4775a2ff224dfd
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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