Phosphorus pentachloride → 1-(but-3-enyl)-6-chloro-N-(2,6-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-amine

HRID 2357980Notes

Reaction equation

HRID 2357980 reaction equation
[CH2:1]([N:5]([C:7]1[C:12]([C:13]([NH:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])=O)=[CH:11][N:10]=[C:9]([Cl:24])[N:8]=1)[NH2:6])[CH2:2][CH:3]=[CH2:4].P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:7]2=[N:8][C:9]([Cl:24])=[N:10][CH:11]=[C:12]2[C:13]([NH:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])=[N:6]1)[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 588368794-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

Product 1

HCID 588368811-(but-3-enyl)-6-chloro-N-(2,6-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3.42 g (9.9 mmol) of 4-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide 31 (Example 1, Step C) in 100 mL of toluene was treated with 2.16 g (95%, 9.9 mmol) of phosphorus pentachloride. The resulting orange slurry was heated at 100° C. for 1.75 h, and then was concentrated. The residue was dissolved in CH2Cl2 (250 mL) and washed with saturated aqueous sodium bicarbonate (150 mL). The aqueous layer was extracted with more CH2Cl2 (100 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound 32. 1H-NMR (CDCl3) δ 2.24 (s, 6H), 2.62-2.68 (m, 2H), 4.31 (t, J=7.2 Hz, 2H), 4.99 (dd, J=10.2 Hz, 1.6 Hz, 1H), 5.05 (dd, J=17.1 Hz, 1.6 Hz, 1H), 5.72-5.83 (m, 1H), 6.06 (s, 1H), 7.13-7.22 (m, 3H), 7.58 (s, 1H). Mass Spectrum (ESI) m/e=328.1 (M+1).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2 (250 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (150 mL)
  4. extractionThe aqueous layer was extracted with more CH2Cl2 (100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate was purified by chromatography on silica gel (hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-8a8f8c703fc74542b4ffc813b4528fd8
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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