Diisobutylaluminum hydride → 2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol

HRID 528449Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[C:8]([Cl:20])=[N:9][C:10]([Cl:19])=[N:11][C:12]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)C.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:19][C:10]1[N:9]=[C:8]([Cl:20])[C:7]([O:6][CH2:5][CH2:4][OH:3])=[C:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl ester (188 mg, 0.56 mmol) in THF (2.5 mL) at −78° C. was added DIBAL-H (2.0 mL, 2.0 mmol, 1M solution in THF) and the resulting mixture warmed to 0° C. over 30 minutes. The reaction mixture was quenched with methanol and Rochelle's salt (1M aqueous solution) and the aqueous extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo affording 2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol as an oil (156 mg, 95%). LCMS: RT=2.60 min, [M+H]+=294/296/298.

Workup

customThe reaction mixture was quenched with methanol and Rochelle's salt (1M aqueous solution)
extractionthe aqueous extracted with ethyl acetate
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-923bbcd7db49403fb12e2a09e4ce8b8a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346817B2

Reaction notes

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