Diisobutylaluminum hydride → 2-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-ol

HRID 1192428Notes

Reaction equation

HRID 1192428 reaction equation
C[O:2][C:3](=O)[CH:4]([C:6]1[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=1[Cl:12])[CH3:5].CC(C[AlH]CC(C)C)C>CCOCC>[Cl:12][C:11]1[C:6]([CH:4]([CH3:5])[CH2:3][OH:2])=[C:7]([Cl:13])[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86598738Methyl 4,6-dichloro-alpha-methyl-5-pyrimidineacetate

Product 1

HCID 865987392-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-olYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-(4,6-Dichloro-pyrimidin-5-yl)-propionic acid methyl ester (0.5 g, 2.13 mmol) in ether (40 mL) at −78° C. was added DIBAL-H (1.5M, 4 mL, 6.0 mmol) dropwise. The mixture was allowed to warm up to room temperature and stirred for 3 hours. Then quenched with 2N HCl (10 mL) at −78° C. The aqueous phase was extracted with ethyl acetate (3×50 mL). The organic phase was dried and concentrated. The residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give 2-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-ol (0.40 g, 91%). 1H NMR (CDCl3, 400 MHz) δ 8.62 (s, 1H), 4.16 (m, 1H), 3.90 (m, 2H), 1.93 (s, 1H), 1.40 (d, J=7.2 Hz, 3H).

Workup

  1. customThen quenched with 2N HCl (10 mL) at −78° C
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. washeluted by hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-bbbdcaa0601547f4bbda3392dc25c188
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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