Diisobutylaluminum hydride → (3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)methanol

HRID 2197450Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:27])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20](OC)=[O:21].CC(C[AlH]CC(C)C)C>O1CCCC1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:27])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH2:20][OH:21])[CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of Compound (5) (3.35 g, 7.67 mmol) in THF (“tetrahydrofuran”) (20 mL) cooled to 0° C. was added a 1 M solution of DIBAL-H (34.5 mL, 34.52 mmol) in toluene. The reaction temperature was maintained at 0° C. for 2 h but little progress in the reaction was observed. Additional equivalents (7.6 mL) of DIBAL-H were added at 2 and 4 hours respectively. The DIBAL-H reagent was quenched with 1N HCl, and the quenched reaction mixture was extracted with dichloromethane (3×50 mL) and dried over Na2SO3. Evaporation of the solvent gave 38 g (70%) of Compound (6) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 3.42 (s, 3H), 3.74 (t, J=5.1, 9.9 Hz, 2H), 4.49 (t, J=4.8, 10.2 Hz, 2H), 4.67 (s, 2H), 5.29 (s, 2H), 7.29 (m, 3H), 7.39 (s, 1H). LCMS: m/z for C16H18BrN5O3++H observed 408.1 and 410.0 at 1.85 minutes of a 3.5 minute run, eluting 5-95% CH3CN in H2O (C18 column).

Workup

customThe DIBAL-H reagent was quenched with 1N HCl
customthe quenched reaction mixture
extractionwas extracted with dichloromethane (3×50 mL)
dry with materialdried over Na2SO3
customEvaporation of the solvent

Sources & evidence

ORD record: ord-7ee41f0f871e477f80b11db0e257f63e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338593B2

Reaction notes

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