Phenyl chloroformate → (S)-phenyl 4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenylcarbamate

HRID 1626564Notes

Reaction equation

[CH3:1][N:2]1[CH2:10][C:9]2[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])=[N:7][C:6]([C:18]3[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=3)=[N:5][C:4]=2[CH2:3]1.C([O-])(O)=O.[Na+].Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>C1COCC1>[CH3:1][N:2]1[CH2:10][C:9]2[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])=[N:7][C:6]([C:18]3[CH:24]=[CH:23][C:21]([NH:22][C:31](=[O:32])[O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:20][CH:19]=3)=[N:5][C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirring solution of (S)-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)aniline (intermediate 9) (311 mg, 0.96 mmol) and NaHCO3 (120 mg, 1.43 mmol) in dry THF, was added phenyl chloroformate (133 μL, 1.05 mmol) dropwise. The reaction mixture was stirred at room temperature (20° C.) for 2 hours, before partitioning the crude reaction mixture between water and EtOAc. The phases were separated and the organic layer dried over magnesium sulphate, filtered and then reduced in vacuo, affording the title compound as a pink solid (425 mg, 100%).

Workup

custombefore partitioning the crude
customreaction mixture between water and EtOAc
customThe phases were separated
dry with materialthe organic layer dried over magnesium sulphate
filtrationfiltered

Sources & evidence

ORD record: ord-31596b7b0a6849fab3adbea981014b6a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

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