Acetic Acid → HCID 66735705, compound

HRID 2047221Notes

Reaction equation

HRID 2047221 reaction equation
[NH2:1][CH:2]([C:4]1[CH:9]=[C:8]([N:10]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:7]2[N:27]=[CH:28][CH:29]=[C:6]2[N:5]=1)[CH3:3].[O:30]1[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1.CC(O)=O.[BH3-]C#N.[Na+]>ClCCCl.C(O)C.C(Cl)Cl>[O:30]1[CH2:35][CH2:34][CH:33]([NH:1][CH:2]([C:4]2[CH:9]=[C:8]([N:10]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:18])[CH3:17])[N:7]3[N:27]=[CH:28][CH:29]=[C:6]3[N:5]=2)[CH3:3])[CH2:32][CH2:31]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 66584830HCID 66584830, compound

Product 1

HCID 66735705HCID 66735705, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To crude 5-(1-aminoethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.6 g) in DCE (20 ml) and Ethanol (20 ml) was added tetrahydro-4H-pyran-4-one (0.6 ml, 7 mmol) followed by AcOH (0.08 ml, 1.4 mmol). After stirring for 30 minutes at room temperature, NaBH3CN (0.18 g, 2.8 mmol) was added and stirring was continued further for 30 minutes more. LC/MS showed no starting material (M.W=437) remaining. After the solvent was rotoevaporated, the crude was dissolved with DCM (60 ml), washed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml), dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with MeOH/EtOAC (0-20%) gave desired product, 5-(1-(tetrahydro-2H-pyran-4-ylamino)ethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.2 g, 27%).

Workup

  1. stirringstirring
  2. waitwas continued further for 30 minutes
  3. washwashed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml)
  4. dry with materialdried over MgSO4
  5. customSolvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel
  7. washElution with MeOH/EtOAC (0-20%)

Sources & evidence

ORD record
ord-c240135ab30740728c7c7f9dfb882a2c
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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