Sodium Cyanide → 3-Cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate
Reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[NH:13][C:14]1[N:15]=[CH:16][C:17]2[CH2:22][N:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28]Cl)=[O:24])[CH2:20][C:18]=2[N:19]=1>CN(C)C=O.ClCCl.O.[Cl-].[Li+]>[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[NH:13][C:14]1[N:15]=[CH:16][C:17]2[CH2:22][N:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28][C:1]#[N:2])=[O:24])[CH2:20][C:18]=2[N:19]=1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
Add sodium cyanide (0.230 g; 1.5 equiv; 4.69 mmoles) to a solution containing 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (1.15 g; 1.0 equiv; 3.08 mmoles) in dimethylformamide (10 mL). Heat the reaction mixture to 100° C. for 3 hours, then cool to ambient temperature, dilute with dichloromethane, water, and 5% lithium chloride solution. Separate the layers and further extract the aqueous layer with dichloromethane and ethyl acetate. Dry the combined organic extracts over sodium sulfate, filter, and concentrate to provide 3-cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.98 g; 87%) as a brown solid: MS (m/z): 364(M+1).
Workup
- temperaturecool to ambient temperature
- customSeparate the layers
- extractionfurther extract the aqueous layer with dichloromethane and ethyl acetate
- dry with materialDry the combined organic extracts over sodium sulfate
- filtrationfilter
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-6e61a4b9f9f941f98265ba7396cab2c5
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969555B2
Reaction notes
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