Hydrochloric Acid → 8-{4-[3-(4-Fluoro-phenyl)-prop-2-ynyloxy]-phenyl}-1-propyl-2-(3-trifluoromethyl-phenyl)-1,7-dihydro-purin-6-one

HRID 536003Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:26](COCC[Si](C)(C)C)[C:25]4[C:24](=[O:35])[N:23]([CH2:36][CH2:37][CH3:38])[C:22]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=5)=[N:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.Cl>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[NH:26][C:25]4[C:24](=[O:35])[N:23]([CH2:36][CH2:37][CH3:38])[C:22]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:46])[F:47])[CH:40]=5)=[N:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 8-{4-[3-(4-Fluoro-phenyl)-prop-2-ynyloxy]-phenyl}-1-propyl-2-(3-trifluoromethyl-phenyl)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.056 g, 0.083 mmol), 2N HCl (2 ml), ethanol (2 ml) was heated at 85° C. for 2 hours. The mixture was cooled and the solvent was evaporated. The residue was washed with n-pentane to obtain 8-{4-[3-(4-Fluoro-phenyl)-prop-2-ynyloxy]-phenyl}-1-propyl-2-(3-trifluoromethyl-phenyl)-1,7-dihydro-purin-6-one (0.021 g, 46%) as an off white solid.

Workup

temperatureThe mixture was cooled
customthe solvent was evaporated
washThe residue was washed with n-pentane

Sources & evidence

ORD record: ord-9ee8c824184d4c3c869e48b476738b0c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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