Cesium fluoride → HCID 67046883, compound

HRID 605872Notes

Reaction equation

[Si]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([N:29]2[C:37]([CH3:38])=[N:36][C:35]3[C:30]2=[N:31][C:32]([N:39]2[C:43]4[CH:44]=[C:45]([C:48]#[N:49])[CH:46]=[CH:47][C:42]=4[N:41]=[CH:40]2)=[N:33][CH:34]=3)[CH2:21][CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].[Cs+]>CN(C=O)C>[OH:18][C@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([N:29]2[C:37]([CH3:38])=[N:36][C:35]3[C:30]2=[N:31][C:32]([N:39]2[C:43]4[CH:44]=[C:45]([C:48]#[N:49])[CH:46]=[CH:47][C:42]=4[N:41]=[CH:40]2)=[N:33][CH:34]=3)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

A 50 ml round bottom flask was charged with 0.06 g (0.091 mmol) of 3-(9-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-8-methyl-9H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile. 20 ml of DMF was then added, followed by 0.07 g (0.45 mmol) of Cesium Fluoride, and the resulting mixture was stirred at 50° C. overnight (drying tube was attached to flask). The mixture was cooled to room temp, diluted with 100 ml EtOAc and washed with approx 10 ml water. The organic layer was dried over MgSO4 and concentrated in vacuo, and purified by column chromatography (eluting with 1% MeOH in DCM), to give 0.023 g (60%) of the titled compound.

Workup

custom(drying tube was attached to flask)
temperatureThe mixture was cooled to room temp
additiondiluted with 100 ml EtOAc
washwashed with approx 10 ml water
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
custompurified by column chromatography (eluting with 1% MeOH in DCM)

Sources & evidence

ORD record: ord-c1a5a39fd96a49eca6549f40899b51bf
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915268B2

Reaction notes

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