Water → N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 1269070Notes

Reaction equation

HRID 1269070 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.[CH:82]1([NH2:87])[CH2:86][CH2:85][CH2:84][CH2:83]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:82]1([NH:87][C:2]2[N:7]3[N:8]=[C:9]([C:23]4[O:24][CH:25]=[CH:26][C:27]=4[CH3:28])[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]5[CH2:22][CH2:21][CH2:20][CH2:19]5)[N:12]=4)=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:86][CH2:85][CH2:84][CH2:83]1

Participants

7

Reactant 5

HCID 962WaterHCID 2906CyclopentylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 111768674-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

Product 1

HCID 10127409N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-7-amineYield 87%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[7-chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (150 mg, 0.38 mmol) in cyclopentylamine (10 mL) was added racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (76 mg, 0.12 mmol), cesium carbonate (247 mg, 0.76 mmol) and palladium (II) acetate (17 mg, 0.076 mmol). The resulting mixture was stirred at 100° C. for 3 hours. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (3:7 ethyl acetate:hexane) to give 147 mg (87%) of N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-7-amine as a yellow solid. 1H-NMR (CDCl3): δ 8.07 (d, 1H), 7.85 (d, 1H), 7.50 (d, 1H), 7.31 (t, 1H), 6.42 (d, 1H), 6.25 (d, 1H), 6.04 (d, 1H), 6.00 (d, 1H), 5.06 (d, 1H), 4.36 (m, 1H), 3.98 (m, 1H), 2.08 (m, 4H), 2.05 (s, 3H), 1.81–1.52 (m, 12H). MS m/z 443 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash chromatography (3:7 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-0ba15833f72348ff8281290f36a6f378
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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