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

HRID 1626644Notes

Reaction equation

HRID 1626644 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.[N:30]([CH:33]1[CH2:35][CH2:34]1)=[C:31]=[O:32]>>[CH:33]1([NH:30][C:31](=[O:32])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]=[C:10]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]4[CH3:28])[C:11]4[CH2:16][N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][C:12]=4[N:13]=3)=[C:4]([F:29])[CH:3]=2)[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 637659IsocyanatocyclopropaneHCID 66679046(S)-ethyl 2-(4-amino-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Product 1

HCID 66679208(S)-ethyl 2-(4-(3-cyclopropylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 47%

Procedure

Method as example 113 step 2 using (S)-ethyl 2-(4-amino-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate and isocyanatocyclopropane as starting materials. The solvent was removed in vacuo and the residue purified by prep HPLC (low pH) yielding the final compound (17 mg, 0.04 mmol, 47%).

Workup

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

Sources & evidence

ORD record
ord-e26e370a209f473982f60a699ea2dd8f
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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