p-Toluenesulfonic acid → (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea
Reaction equation
[CH:1]1([NH:4][C:5](=[O:36])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]4[CH3:35])[C:16]4[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C:17]=4[N:18]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CO>[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]4[CH3:35])[C:16]4[CH2:21][NH:20][CH2:19][C:17]=4[N:18]=3)=[CH:11][CH:12]=2)=[O:36])[CH2:2][CH2:3]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
To a stirred solution of (S)-tert-butyl 2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (0.99 g, 1.99 mmol) in DCM (5 mL) was added TFA (2.5 mL) and stirred at room temperature (20° C.) overnight. The reaction mixture was diluted with methanol and adsorbed onto a mp-TsOH cartridge (2.5 g, 3 mmol/g). The cartridge was rinsed with MeOH (3 column volumes) and the product was eluted with 7M NH3 in MeOH. The basic fractions were concentrated in vacuo to leave a pale orange solid (0.46 g, 1.16 mmol, 58% yield).
Workup
- washThe cartridge was rinsed with MeOH (3 column volumes)
- washthe product was eluted with 7M NH3 in MeOH
- concentrationThe basic fractions were concentrated in vacuo
Sources & evidence
- ORD record
- ord-60b14d6ddd554a00bf2e59a2bb3e6342
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785457B2
Reaction notes
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