N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine → N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-isobutylpyrazolo[1,5-a]pyridin-7-amine

HRID 859974Notes

Reaction equation

HRID 859974 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH2:25][CH:26]([CH3:28])[CH3:27])=[N:15][N:16]4[C:21](S(C)=O)=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1(N)CCCC1>[CH:1]1([NH:6][C:21]2[N:16]3[N:15]=[C:14]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:13]([C:11]4[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)[N:12]=4)=[C:17]3[CH:18]=[CH:19][CH:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 10453435N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine

Product 1

HCID 10454730N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-isobutylpyrazolo[1,5-a]pyridin-7-amineYield 158.7%

Reagents, catalysts & solvents 1

HCID 2906CyclopentylamineSolvent

Procedure

A solution of N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine (110 mg, 0.28 mmol) in cyclopentylamine (5 mL) was heated at 130° C. for 72 h. The mixture was cooled to room temperature and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (hexane-ethyl acetate) to give N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-isobutylpyrazolo[1,5-a]pyridin-7-amine (93 mg, 81%) as a White solid. 1H NMR (CDCl3) δ 8.20 (d, 1H), 7.50 (d, 1H), 7.21 (t, 1H), 6.74 (d, 1H), 5.97–5.92 (m, 2H), 5.09 (d, 1H), 4.38 (m, 1H), 3.96 (m, 1H), 3.01 (d, 2H), 2.27–2.04 (m, 5H), 1.81–1.50 (m, 12H), 0.97 (d, 6H); MS m/z 419 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by flash chromatography on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2fb9e164d86b422888b6ded3ec3a2a38
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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