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Diisopropylethylamine → 3-[3-(Tert-butoxycarbonylamino)propionyl]amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

HRID 1247800
Notes
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Reaction equation

HRID 1247800 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]2[CH2:15][CH2:14][CH2:13][NH:12][C:11]=12.C(N(C(C)C)C(C)C)C.[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][C:35](ON1C(=O)CCC1=O)=[O:36])=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][C:35]([NH:6][C:7]1[CH:8]=[N:9][N:10]2[CH2:15][CH2:14][CH2:13][NH:12][C:11]=12)=[O:36])=[O:31])([CH3:28])([CH3:27])[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10684599Boc-Beta-Ala-OSuHCID 1358007334,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidin-3-amine sulfate

Product 1

HCID 1358007343-[3-(Tert-butoxycarbonylamino)propionyl]amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 3-amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine sulfuric acid salt (4.44 g) and N-ethyldiisopropylamine (3.88 g) in methylene chloride (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (4.29 g). The mixture was stirred at room temperature for 6 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution. 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-(tert-butoxycarbonylamino)propionyl]amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (3.67 g) as an oil.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-88ecec24816a4c4d82a1aefa02972ad2
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07129232B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes