Diisobutylaluminumhydride → HCID 68439304, compound

HRID 1853443Notes

Reaction equation

HRID 1853443 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[N:10][CH:11]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH3:23][C:7]1[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[N:8]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68439408HCID 68439408, compound

Product 1

HCID 68439304HCID 68439304, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carboxylic acid ethyl ester (0.20 g, 0.63 mmol) in THF (6 mL) was added diisobutylaluminum hydride (1 M in hexanes; 1.25 mL, 1.25 mmol) dropwise. The mixture was warmed to rt over 1 h. The reaction was quenched with 1 M H2SO4 (2 mL). The mixture was neutralized with satd. aq. NaHCO3, and diluted with MeOH (2 mL), CHCl3 (10 mL), and satd. aq. sodium potassium tartrate (10 mL). The mixture was stirred vigourously until the layers separated. The organic layer was dried (Na2SO4) and concentrated to give the crude product (138 mg), which was used in the next step without further purification. 1H NMR (CDCl3): 8.07 (s, 1H), 4.52 (s, 2H), 3.42-3.33 (m, 2H), 2.88-2.74 (m, 2H), 2.41 (s, 3H), 2.23 (s, 3H), 1.93-1.83 (m, 2H), 1.72-1.53 (m, 4H), 1.35-1.16 (m, 5H).

Workup

  1. customThe reaction was quenched with 1 M H2SO4 (2 mL)
  2. additionaq. NaHCO3, and diluted with MeOH (2 mL), CHCl3 (10 mL)
  3. customseparated
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e2bf0c3c7a374b4cbfd4ce878dcd20c9
Source dataset
uspto-grants-2015_02
Patent number
US08962644B2

Reaction notes

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