Tetrahydrofuran → HCID 60198532, compound

Reaction equation

[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20]([N:22]1[CH2:31][CH2:30][C:29]2[CH:28]=[N:27][C:26]([NH:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[N:25][C:24]=2[CH2:23]1)=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=1)(C(C)(C)C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[Cl:18][C:13]1[CH:12]=[C:11]([C@H:10]([NH:19][C:20]([N:22]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][C:26]([NH:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[N:25][C:24]=3[CH2:23]2)=[O:21])[CH2:9][OH:8])[CH:16]=[CH:15][C:14]=1[F:17]

Participants

Procedure

To a solution of (S)—N-(2-(tert-butyldimethylsilyloxy)-1-(3-chloro-4-fluorophenyl)ethyl)-2-(tetrahydro-2H-pyran-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide (0.250 g, 0.443 mmol) and THF (5 mL) at RT was added TBAF (0.532 mL, 0.532 mmol) and the reaction was stirred for 1 h at RT, poured into water and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:20 to 500:30) to afford 0.100 g (50.2%) of I-46: 1H NMR (400 MHz, d6-DMSO) δ 8.08 (s, 1H), 7.52 (d, 1H), 7.32 (d, 2H), 6.91-6.86 (m, 2H), 4.85 (br s, 1H), 4.74 (m, 1H), 4.40-4.30 (m, 2H), 3.87-3.84 (m, 3H), 3.58-3.54 (m, 4H), 3.38-3.31 (m, 2H), 2.56-2.54 (m, 2H), 1.81-1.78 (m, 2H), 1.53-1.46 (m, 2H); MS m/z (APCI-pos) M+1=450.