Dichloromethane → 2-Ethyl-5,7-dimethyl-3-[4-(piperidin-4-ylmethoxy)-benzyl]-pyrazolo[1,5-a]pyrimidine hydrochloride

HRID 403514Notes

Reaction equation

HRID 403514 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].C([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35]O)[CH2:31][CH2:30]1)(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:70]CCl>C(OC(=O)C)C>[ClH:70].[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:35][CH:32]3[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]3)=[CH:19][CH:20]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 683792244-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

Product 1

HCID 683792882-Ethyl-5,7-dimethyl-3-[4-(piperidin-4-ylmethoxy)-benzyl]-pyrazolo[1,5-a]pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenol (8), (0.12 g, 0.4 mmol) N-Boc-4-piperidinmethanol (0.11 g, 0.49 mmol) were dissolved in 3 ml of dichloromethane and triphenylphosphine (0.13 g, 0.49 mmol) and DIAD (0.12 g, 0.49 mmol) were added. The reaction mixture was stirred at rt for 12 h. It was then diluted with ethylacetate and the organic layer was washed with 5% aqueous NaHCO3 solution. The organic layer was washed again with brine and dried over Na2 SO4. It was then concentrated under reduced pressure and the crude product purified by chromatography to give the title compound as a white solid. Boc deprotection was performed analogously to example 3 step B.

Workup

  1. washthe organic layer was washed with 5% aqueous NaHCO3 solution
  2. washThe organic layer was washed again with brine
  3. customdried over Na2 SO4
  4. concentrationIt was then concentrated under reduced pressure
  5. customthe crude product purified by chromatography

Sources & evidence

ORD record
ord-67eaf6fdd17f4eb7bd31175dc18f5e7b
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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