Diisobutylaluminumhydride → HCID 66955971, compound

HRID 1399726Notes

Reaction equation

HRID 1399726 reaction equation
[CH3:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:5]=[C:4]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[N:5]=[C:4]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[N:3]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66955386HCID 66955386, compound

Product 1

HCID 66955971HCID 66955971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidine-5-carboxylate (2 g; 5,89 mmol) in dry dichloromethane (20 mL) at (−78° C.) under nitrogen atmosphere was slowly added a solution of diisobutylaluminium hydride (1M in dichloromethane) (13 mL; 13 mmol) and the reaction was stirred for 1 h at (−78° C.), then allowed to warm up to 0° C. and the stirring was carried on 2 h more. The reaction was quenched by adding a solution of hydrochloric acid 1N and the mixture was vigorously stirred for 1 h. The phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium potassium tartrate and brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The desired compound was obtained as a white solid (1.48 g; 84%) and used as such in the next step.

Workup

  1. temperatureto warm up to 0° C.
  2. waitthe stirring was carried on 2 h
  3. customThe reaction was quenched
  4. additionby adding a solution of hydrochloric acid 1N
  5. stirringthe mixture was vigorously stirred for 1 h
  6. customThe phases were separated
  7. extractionthe aqueous layer was extracted with dichloromethane
  8. washThe combined organic layers were washed with a saturated solution of sodium potassium tartrate and brine
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d6a010208214760a632e5c4deaaaba2
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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