Boron tribromide → 4-{7-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenol

HRID 861111Notes

Reaction equation

HRID 861111 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10298785N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-methoxyphenyl)-pyrazolo[1,5-a]pyridin-7-amine

Product 1

HCID 1354695774-{7-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine (1.16 g, 2.48 mmol) in dichloromethane (50 mL) at −78° C. was added boron tribromide (9.92 mL, 1.0 M in dichloromethane, 9.92 mmol) dropwise. The resulting solution was allowed to warm to room temperature. After stirring for 15 hours at room temperature, the mixture was cooled to 0° C. and quenched by the addition of water. The mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated to give a solid residue which was purified by flash chromatography (95:5 chloroform-methanol). 4-{7-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenol was obtained as a yellow solid (0.80 g, 71%). 1H NMR (CDCl3): δ 7.91 (d, 1H), 7.70 (d, 1H), 7.46 (d, 2H), 7.26 (t, 1H), 6.86 (d, 2H), 6.27 (d, 1H), 6.00–5.97 (m, 2H), 5.06 (d, 1H), 4.33 (m, 1H), 3.96 (m, 1H), 2.10–2.03 (m, 4H), 1.78–1.47 (m, 12H); MS m/z 455 (M+1). U157430-190

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customquenched by the addition of water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid residue which
  8. customwas purified by flash chromatography (95:5 chloroform-methanol)

Sources & evidence

ORD record
ord-6c77a6d04d9b43adb9dcaa2dab9a8b28
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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