Trifluoroacetic acid methylene chloride → HCID 66970651, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([NH:16][C:17]2[N:25]=[C:24]3[C:20]([NH:21][C:22](=[O:36])[N:23]3[C:26]3[CH:27]=[C:28]4[C:33](=[CH:34][CH:35]=3)[NH:32][CH2:31][CH2:30][CH2:29]4)=[CH:19][N:18]=2)[CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:16][C:17]1[N:25]=[C:24]2[C:20]([NH:21][C:22](=[O:36])[N:23]2[C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[NH:32][CH2:31][CH2:30][CH2:29]3)=[CH:19][N:18]=1Participants
Procedure
A solution of tert-butyl 4-fluoro-2-(8-oxo-9-(1,2,3,4-tetrahydroquinolin-6-yl)-8,9-dihydro-7H-purin-2-ylamino)phenylcarbamate (obtained from tert-butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidine-2-ylamino)phenylcarbamate and 1,2,3,4-tetrahydroquinolin-6-amine (J. Org. Chem. (2002), 67, 7890) using procedures outlined in Example 27) was stirred for 45 minutes in 1:1 TFA/DCM and concentrated to afford 2-(2-amino-5-fluorophenylamino)-9-(1,2,3,4-tetrahydroquinolin-6-yl)-7H-purin-8(9H)-one. The 2-(2-amino-5-fluorophenylamino)-9-(1,2,3,4-tetrahydroquinolin-6-yl)-7H-purin-8(9H)-one was stirred for 15 minutes in trimethylorthoformate and concentrated to afford 6-(2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-7,8-dihydropurin-9-yl)-3,4-dihydroquinoline-1(2H)-carbaldehyde, which was purified by silica gel chromatography (2→5% MeOH in DCM). This material was deformylated by refluxing for 1 hour in 11:2 1 M HCl:MeOH to provide the title compound as the HCl salt. 1H-NMR (300 MHz, CD3OD) δ 10.0 (s, 1H), 8.4 (s, 1H), 8.4 (dd, 1H), 7.8 (dd, 1H), 7.8 (s, 1H), 7.8 (d, 1H), 7.5 (d, 1H), 7.4 (td, 1H), 3.6 (dd, 2H), 3.1 (t, 2H), 2.2 (m, 2H).
Workup
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d25102282e5844779e23be0d037baabc
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884109B2
Reaction notes
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