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

HRID 1626627Notes

Reaction equation

HRID 1626627 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)=[C:4]([F:29])[CH:3]=1.[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])=[CH:3][C:4]=3[F:29])=[N:13][C:12]=2[CH2:14]1)=[O:18])[CH3:21]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 66679046(S)-ethyl 2-(4-amino-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Product 1

HCID 66679040(S)-ethyl-2-(4-(3-ethylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 34%

Procedure

Method as example 85 using (S)-ethyl 2-(4-amino-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate and ethyl isocyanate as starting materials. The solvent was removed in vacuo and purified by prep HPLC (low pH) yielding the title compound (14.6 mg, 0.03 mmol, 34%).

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-3d1ab96f746349459c4531aaec7a03ff
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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