1,1'-Carbonyldiimidazole → 3-(3-{2-[(Tert-butoxycarbonyl)amino]ethyl)ureido)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine
Reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(N(C(C)C)C(C)C)C.S(=O)(=O)(O)O.N[C:39]1[CH:40]=[N:41][N:42]2CCCN[C:43]=12>C(Cl)Cl>[C:19]([O:18][C:17]([NH:16][CH2:15][CH2:14][NH:13][C:1](=[O:2])[NH:8][C:12]1[CH:40]=[N:41][N:42]2[CH2:43][CH2:39][CH2:9][NH:10][C:11]=12)=[O:23])([CH3:20])([CH3:22])[CH3:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 1,1′-carbonyldiimidazole (973 mg) in methylene chloride (10 ml) was added tert-butyl N-(2-aminoethyl)carbamate (1.11 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added N-ethyldiisopropylamine (1.28 g) and 3-amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine sulfuric acid salt (1.18 g), and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform to give 3-(3-{2-[(tert-butoxycarbonyl)amino]ethyl}ureido)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (150 mg) as a solid.
Workup
- temperaturecooling
- stirringthe mixture was stirred at 50° C. for 6 hours
- washThe reaction mixture was washed with brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform
Sources & evidence
- ORD record
- ord-2e8b234ab8dd449e8f2eb8dd153433d7
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129232B2
Reaction notes
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