3-Pyridinemethanol → HCID 58063073, compound

HRID 474326Notes

Reaction equation

HRID 474326 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].Cl[C:20]1[N:25]=[CH:24][N:23]2[N:26]=[CH:27][C:28]([C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])=[C:22]2[CH:21]=1>CN(C=O)C>[CH:32]([NH:31][C:29]([C:28]1[CH:27]=[N:26][N:23]2[CH:22]=[CH:21][C:20]([O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:25][C:24]=12)=[O:30])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 2733832Lithium HexamethyldisilazideHCID 86661440HCID 86661440, compound

Product 1

HCID 58063073HCID 58063073, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a degassed solution of 3-pyridylcarbinol (17.6 mg, 0.16 mM, 1.5 equiv) in 0.8 mL of DMF was added a one molar solution of lithium hexamethyldisilazide (215 uL, 0.22 mM, 2.0 equiv). This mixture was stirred for 10 minutes then added dropwise to a stirred solution of 5-chloro-N-isopropylpyrazolo[1,5-c]pyrimidine-3-carboxamide (25.7 mg, 0.11 mM, 1.0 equiv) in one mL of DMF. The reaction mixture was purified using reversed phase HPLC (5 to 30% acetonitrile/water, 0.1% formic acid) and the product lyophilized to give 22.7 mg (68%) of N-isopropyl-5-(pyridin-3-ylmethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=312.2, 1H NMR (400 MHz, DMSO-d6) δ: 9.09 (d, 1H), 8.76 (d, 1H), 8.59 (dd, 1H), 8.38 (s, 1H), 7.95 (d, 1H), 7.45 (dd 2H), 6.81 (d, 1H), 5.61 (s, 1H), 4.08 (m, 1H), 1.19 (d, 6H).

Workup

  1. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-6cf154564cbc4fb888df61b4e1a21b47
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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