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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 1626599
Notes
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Reaction equation

HRID 1626599 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 66679018(S)-2-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)aniline2×

Product 1

HCID 66678772(S)-1-ethyl-3-(2-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureaYield 14.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes