Ethyl isocyanate → (S)-ethyl-2-(4-(3-ethylureido)-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626614Notes

Reaction equation

HRID 1626614 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:11]3[CH2:16][N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][C:12]=3[N:13]=2)=[CH:4][C:3]=1[F:29].[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31]>>[CH2:20]([O:19][C:17]([N:15]1[CH2:16][C:11]2[C:10]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])=[N:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:33]([NH:32][CH2:30][CH3:31])=[O:34])=[C:3]([F:29])[CH:4]=3)=[N:13][C:12]=2[CH2:14]1)=[O:18])[CH3:21]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 66679065(S)-ethyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate2×

Product 1

HCID 66679183(S)-ethyl-2-(4-(3-ethylureido)-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 22%

Procedure

Method as described for example 85 using (S)-ethyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 19) and ethyl isocyanate as starting materials. The solvent was removed in vacuo and the residue purified by prep HPLC (high pH) yielding the title compound (10 mg, 0.021 mmol, 22%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by prep HPLC (high pH)

Sources & evidence

ORD record
ord-06d8c94e422d4a72a249851394fc32a1
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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