Hydrochloric Acid → 6-[(1S)-2-amino-1-benzyl-ethyl]-2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one
Reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([O:11]CC)=O)=[CH:7][N:6]=[C:5]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][C:15]=2[Cl:20])[N:4]=1.C(OC(=O)[NH:27][CH2:28][C@@H:29]([NH2:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(C)(C)C.C(N(CC)C(C)C)(C)C.Cl>C(O)CCC.C1COCC1>[NH2:27][CH2:28][C@@H:29]([N:37]1[C:9](=[O:11])[C:8]2[CH:7]=[N:6][C:5]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[Cl:20])=[N:4][C:3]=2[CH2:2]1)[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
A mixture of ethyl 4-(bromomethyl)-2-(4-chloro-1-methyl-1H-pyrazol-5-yl)pyrimidine-5-carboxylate (284.0 mg, 0.7898 mmol), tert-butyl[(2S)-2-amino-3-phenylpropyl]carbamate (198 mg, 0.791 mmol), and N,N-diisopropylethylamine (0.275 mL, 1.58 mmol) in 1-butanol (5.0 mL) was stirred at 140° C. for 2 h. The reaction mixture was evaporated under reduced pressure to give an oil residue, which was dissolved in 4 M HCl aqueous solution (2 mL, 8 mmol) and THF (2 mL). The resulting solution was stirred at room temperature for 1 hour. Direct purification on prep.HPLC afforded 81 mg (25.6% yield) of the desired product. LC-MS found: 383.1 (M+H)+.
Workup
- customThe reaction mixture was evaporated under reduced pressure
- customto give an oil residue, which
- stirringThe resulting solution was stirred at room temperature for 1 hour
- customDirect purification on prep.HPLC
Sources & evidence
- ORD record
- ord-c4d9ee2c8ca146a6aa4171f04e6ec69a
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895571B2
Reaction notes
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