Lithium Hydroxide → HCID 178441725, compound

HRID 1182824Notes

Reaction equation

[O:1]1[CH2:5]CCC1.C(OC[CH2:11][O:12][C:13]1[CH:14]=[N:15][C:16]([N:19]2[C:24](=[O:25])[C:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[NH:43][N:42]=[N:41][N:40]=4)=[CH:29][CH:28]=3)=[C:22]([CH2:44][CH2:45][CH2:46][CH3:47])[N:21]=[C:20]2[CH3:48])=[N:17][CH:18]=1)(=O)C.[OH-:49].[Li+]>O>[NH:40]1[C:39]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[C:30]2[CH:31]=[CH:32][C:27]([CH2:26][C:23]3[C:24](=[O:25])[N:19]([C:16]4[N:17]=[CH:18][C:13]([O:12][CH2:11][C:5]([OH:1])=[O:49])=[CH:14][N:15]=4)[C:20]([CH3:48])=[N:21][C:22]=3[CH2:44][CH2:45][CH2:46][CH3:47])=[CH:28][CH:29]=2)=[N:43][N:42]=[N:41]1

Participants

Conditions

Temperature: 50 °C

Procedure

To the mixture solution of tetrahydrofuran (2 mL) and water (2 mL) containing 2-{2-(5-{[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-4-butyl-2-methyl-6-oxopyrimidin-1 (6H)-yl)pyrimidin-5-yl oxy}ethyl acetate (22 mg, 0.038 mmol), lithium hydroxide (8 mg, 0.29 mmol) was added and stirred at 50° C. for 1 hr. The reaction mixture was added water and extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (chloroform/methanol) to obtain the target compound (15 mg, 72%) as a white solid.

Workup

additionwas added
extractionextracted with chloroform
washwashed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f038164630b34a819551ab5949cccf23
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664226B2

Reaction notes

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