Tetrahydrofuran → HCID 178518657, compound

HRID 1363212Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:29])[N:16]4[C@H:19]4[CH2:24][CH2:23][C@H:22]([C:25](OC)=[O:26])[CH2:21][CH2:20]4)=[CH:12][N:11]=3)[C:6]=2[CH:30]=1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:29])[N:16]4[C@H:19]4[CH2:20][CH2:21][C@H:22]([CH2:25][OH:26])[CH2:23][CH2:24]4)=[CH:12][N:11]=3)[C:6]=2[CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of trans-methyl 4-(2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-7,8-dihydropurin-9-yl)cyclohexanecarboxylate (6 mg) in DCM was treated with 10 equivalents of a 1 M THF solution of LiAlH4 at −10° C. The mixture was stirred at −10° C. for 12 hours and 0° C. for 2 more hours. The mixture was quenched with aqueous sodium bicarbonate and extracted with EtOAc. Silica gel chromatography provided 3.0 mg of the title compound. 1H-NMR (300 MHz, CDCl3) δ 9.0 (s, 1H), 8.3 (dd, 1H), 8.1 (s, 1H), 7.7 (dd, 1H), 7.1 (td, 1H), 4.3 (m, 1H), 3.3 (d, 2H), 2.4 (m, 2H), 1.9 (m, 4H), 1.6 (m, 2H).

Workup

customThe mixture was quenched with aqueous sodium bicarbonate
extractionextracted with EtOAc

Sources & evidence

ORD record: ord-20033c34e012408ab71a25dd2957877c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884109B2

Reaction notes

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