Carbon Dioxide → HCID 22250825, compound

HRID 890423Notes

Reaction equation

HRID 890423 reaction equation
C(=O)=O.C([O:6][C:7]([C:9]1[C:10]([CH3:25])=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)=O)C.CC(C[AlH]CC(C)C)C.Cl>C1COCC1.C1(C)C=CC=CC=1>[CH3:25][C:10]1[C:9]([CH2:7][OH:6])=[CH:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)[N:11]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 69637672HCID 69637672, compound

Product 1

HCID 22250825HCID 22250825, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a dry ice chilled solution of 1.66 g (5.35 mmol) 4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester in 20 ml THF was dropped at −70° C. 12.35 ml (16.05 mmol) 1.2M DIBALH solution in toluene. The reaction mixture was stirred 1 h at −70° C. and after attaining RT the reaction was stirred for another 2 h at this temperature. A solution of 50 ml of 1N HCl was added dropwise, then the reaction mixture partitioned between ether and water. The ether solution was concentrated under reduced pressure to provide 1.42 g of pure [4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol.

Workup

  1. customafter attaining RT
  2. stirringwas stirred for another 2 h at this temperature
  3. customthe reaction mixture partitioned between ether and water
  4. concentrationThe ether solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0dba3f1bf644fe2ab075fc9e8dd2e4b
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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