Tetrabutylammonium Fluoride → HCID 71715824, compound

HRID 538931Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]2[CH:17]=[C:16]([N:18]3[C@@H:22]([CH3:23])[C@@H:21]([CH2:24][CH2:25][O:26][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[O:20][C:19]3=[O:44])[N:15]=[C:14]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)[N:13]=2)=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]2[CH:17]=[C:16]([N:18]3[C@@H:22]([CH3:23])[C@@H:21]([CH2:24][CH2:25][OH:26])[O:20][C:19]3=[O:44])[N:15]=[C:14]([N:45]3[CH2:46][CH2:47][O:48][CH2:49][CH2:50]3)[N:13]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (4S,5R)-3-(2′-amino-2-morpholino-4′-(trifluoromethyl)-[4,5′-bipyrimidin]-6-yl)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyloxazolidin-2-one (2.1 g, 3 mmol) in THF (20 mL), was added dropwise 1M TBAF in THF (3 mL, 3 mmol) at 0° C. The reaction mixture was stirred for 1 h at 0° C. before evaporation. The residue was purified by flash chromatography (hexane/EtOAc/MeOH 90:10:1→0:100:10). The purified product was re-crystallized from MeOH to afford the title compound as a white solid (1.17 g, 83%): tR=0.80 min (UPLC 1), tR=0.82 min (LC-MS 3); ESI-MS: 470 [M+H]+ (LC-MS 3).

Workup

customThe residue was purified by flash chromatography (hexane/EtOAc/MeOH 90:10:1→0:100:10)
customThe purified product was re-crystallized from MeOH

Sources & evidence

ORD record: ord-ef362df8b4eb411cbfd9f465de4186f8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865894B2

Reaction notes

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