Dimethyl Carbonate → Methyl 2-[(3,4,5-trimethoxyphenyl)amino]-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[CH2:23][NH:22][CH2:21]C[C:18]=3[N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:24](=[O:29])([O:27][CH3:28])OC.C(N(C(C)C)CC)(C)C>C1COCC1.CCOC(C)=O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([NH:13][C:14]2[N:19]=[CH:18][C:17]3[CH2:23][N:22]([C:24]([O:27][CH3:28])=[O:29])[CH2:21][C:16]=3[N:15]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A solution of N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (0.020 g, 0.063 mmol) in anhydrous THF (2.0 mL) was treated sequentially with dimethyl carbonate (0.006 g, 0.063 mmol) and diisopropylethylamine (0.025 mL, 0.095 mmol). The reaction was heated to 60° C. and allowed to stir for 5 hours. The reaction was cooled to room temperature, then diluted with EtOAc and washed three times with brine. The combined aqueous layers were then washed twice with EtOAc. The organic layers were combined, dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was then purified over silica using a EtOAc/Hexanes gradient affording the final product in 64% yield (0.015 g, 0.040 mmol).
Workup
- temperatureThe reaction was cooled to room temperature
- washwashed three times with brine
- washThe combined aqueous layers were then washed twice with EtOAc
- dry with materialdried over anhydrous Na2SO4(s)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was then purified over silica using a EtOAc/Hexanes gradient
Sources & evidence
- ORD record
- ord-d9beb289269c4e369e2e543d27b3bffb
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296747B1
Reaction notes
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