Ethyl isocyanate → (S)-1-ethyl-3-(2-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626599Notes

Reaction equation

[F:1][C:2]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[C:12]3[CH2:17][N:16]([CH3:18])[CH2:15][C:13]=3[N:14]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27]>C1COCC1>[CH2:26]([NH:28][C:29]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([C:9]2[N:10]=[C:11]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[C:12]3[CH2:17][N:16]([CH3:18])[CH2:15][C:13]=3[N:14]=2)=[CH:8][C:2]=1[F:1])=[O:30])[CH3:27]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of (S)-2-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)aniline (intermediate 16) (139 mg, 0.40 mmol) in dry THF, was added ethyl isocyanate (70 μL, 0.89 mmol) dropwise. The reaction mixture was stirred at 40° C. for 48 hours, before removal of the solvent in vacuo. The crude material was then purified prep. HPLC (high pH), affording the title compound as a white solid (23.3 mg, 13.7%).

Workup

customThe crude material was then purified prep

Sources & evidence

ORD record: ord-35c05fffdd0443cba3b0d2985d67d166
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

Loading…