Ammonia methanol → HCID 58109315, compound

HRID 2046001Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@@:19]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)([CH2:22][CH2:23][CH2:24][OH:25])[O:18][C:17]3=[O:33])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.CO.[NH3:36]>>[NH2:36][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@@:19]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)([CH2:22][CH2:23][CH2:24][OH:25])[O:18][C:17]3=[O:33])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 58109263HCID 58109263, compound

Product 1

HCID 58109315HCID 58109315, compoundYield 90%

Conditions

Temperature: 90 °C

Procedure

(R)-3-((S)-1-(4-(2-chloropyrimidin-4-yl)phenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (300 mg, 0.6 mmol) was dissolved in MeOH/NH3 (10 mL). The resulting mixture was heated to 90° C. for 24 h. The mixture was concentrated to give the crude product, which was purified by preparative TLC to give (R)-3-((S)-1-(4-(2-aminopyrimidin-4-yl)phenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (270 mg, 90%).

Workup

concentrationThe mixture was concentrated
customto give the crude product, which
customwas purified by preparative TLC

Sources & evidence

ORD record: ord-2b2006a6b72447918acb1a46cd5a6088
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592410B2

Reaction notes

Loading…