Trifluoroacetic acid → 2-(6-Fluoro-1H-benzo[d]imidazol-1-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purine

HRID 1363133Notes

Reaction equation

HRID 1363133 reaction equation
[C:1](O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=O)OC(C)(C)C)=[C:11]([NH:23][C:24]2[N:29]=[C:28]([NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:27]([N+:37]([O-])=O)=[CH:26][N:25]=2)[CH:10]=1>>[F:8][C:9]1[CH:14]=[CH:13][C:12]2[N:15]=[CH:16][N:23]([C:24]3[N:29]=[C:28]4[C:27]([N:37]=[CH:1][N:30]4[CH:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:26][N:25]=3)[C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59705007tert-butyl 4-fluoro-2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)phenylcarbamate

Product 1

HCID 598463902-(6-Fluoro-1H-benzo[d]imidazol-1-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purine

Procedure

The title compound as a TFA salt was synthesized from tert-butyl 4-fluoro-2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)phenylcarbamate via the procedure described in Example 15. 1H NMR (300 MHz, CDCl3): δ 9.73 (s, 1H), 9.29 (s, 1H), 8.5-8.6 (m, 1H), 8.40 (s, 1H), 7.9-8.1 (m, 1H), 7.3-7.4 (m, 1H), 4.8-5.0 (m, 1H), 4.2-4.4 (m, 2H), 3.7-3.8 (m, 2H), 3.05 (d, 1H), 2.2-2.4 (m, 3H). 19F NMR: δ −112.4.

Sources & evidence

ORD record
ord-ccd0d45055bf4a2aaaf179f7891744cb
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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