Diisobutylaluminum hydride → [1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropyl]-methanol

HRID 528467Notes

Reaction equation

C[O:2][C:3]([C:5]1([O:8][C:9]2[C:14]([O:15][CH3:16])=[C:13]([Cl:17])[N:12]=[C:11]([Cl:18])[N:10]=2)[CH2:7][CH2:6]1)=O.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Cl:18][C:11]1[N:10]=[C:9]([O:8][C:5]2([CH2:3][OH:2])[CH2:6][CH2:7]2)[C:14]([O:15][CH3:16])=[C:13]([Cl:17])[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(2,6-dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropanecarboxylic acid methyl ester (293 mg, 1.00 mmol) in DCM (8 mL) at −78° C. was added DIBAL-H (4.00 mL, 4.00 mmol, 1M solution in THF) and the resulting mixture warmed to 0° C. and stirred for 90 minutes. The reaction mixture was quenched with methanol followed by Rochelle's salt (1M aqueous solution) and the mixture extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo affording [1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropyl]-methanol as an oil (220 mg, 83%). LCMS: RT=2.86 min, [M+H]+ 195/197/199.

Workup

customThe reaction mixture was quenched with methanol
extractionthe mixture extracted with ethyl acetate
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-879c267f872a4fe59425e06fb58a1992
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346817B2

Reaction notes

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