Carbon Dioxide → HCID 21935657, compound

HRID 890462Notes

Reaction equation

HRID 890462 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C(=O)=O.C[O:21][C:22]([C:24]1[C:25]([CH2:40][CH2:41][O:42][CH3:43])=[N:26][C:27]([C:30]2[CH:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=2)=[N:28][CH:29]=1)=O.C(OC(C1C(CCOC)=NC(C2C=NC(C(F)(F)F)=CC=2)=NC=1)=O)C>C1COCC1>[CH3:43][O:42][CH2:41][CH2:40][C:25]1[C:24]([CH2:22][OH:21])=[CH:29][N:28]=[C:27]([C:30]2[CH:31]=[N:32][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:34][CH:35]=2)[N:26]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 67072197HCID 67072197, compoundHCID 67072239HCID 67072239, compound

Product 1

HCID 21935657HCID 21935657, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 1.2 M solution of DIBALH in toluene (50 ml, 60 mmol) was dropped within 20 min to a dry ice cooled (−30° C.) solution of 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid methyl ester and 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid ethyl ester (6.83 g, 20 mmol) in THF (100 ml). The reaction mixture was warmed to 0° C., stirred for 1 h at this temperature, the cooling bath was removed and stirring was continued for 1 h at ambient temperature. The mixture was cooled to 0° C., neutralized with aqueous KHSO4 solution (10%) and extracted three times with ether. The combined extracts were washed with aqueous NaCl solution (10%), dried (Na2SO4) and the solvent was removed under reduced pressure. The crude product was crystallized (dichloromethane/ether, 0° C.) to give 6.72 g (21.4 mmol, quant.) [4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl) -pyrimidin-5-yl]-methanol.

Workup

  1. customthe cooling bath was removed
  2. stirringstirring
  3. waitwas continued for 1 h at ambient temperature
  4. temperatureThe mixture was cooled to 0° C.
  5. extractionextracted three times with ether
  6. washThe combined extracts were washed with aqueous NaCl solution (10%)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was removed under reduced pressure
  9. customThe crude product was crystallized (dichloromethane/ether, 0° C.)

Sources & evidence

ORD record
ord-b71637bdf04b48739b21abb7d23a63ea
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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