Carbon Tetrachloride → HCID 10476315, compound

HRID 859980Notes

Reaction equation

HRID 859980 reaction equation
[CH2:1]([C:8]1[C:16]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[N:18]=2)=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].C(Cl)(Cl)(Cl)[Cl:38]>O1CCCC1>[CH2:1]([C:8]1[C:16]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[N:18]=2)=[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([Cl:38])[N:10]2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 2724682Lithium diisopropylamideHCID 9976371HCID 9976371, compound

Product 1

HCID 10476315HCID 10476315, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of 4-(2-benzylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopentyl-2-pyrimidinamine (207 mg, 0.560 mmol) in tetrahydrofuran (7 mL) was added lithium diisopropylamide (17.5 mL, 0.16 M in tetrahydrofuran, 2.80 mmol). The reaction mixture was stirred at −78° C. for 45 minutes, then carbon tetrachloride (542 μl, 5.60 mmol) was added. The reaction mixture was stirred for an additional 30 minutes at −78° C. The reaction mixture was quenched with water, warmed to room temperature, and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (4:1 hexanes:ethyl acetate) provided 4-(2-benzyl-7-chloropyrazolo[1,5-a]pyridin-3-yl)-N-cyclopentyl-2-pyrimidinamine (60 mg, 27%) as a yellow solid. 1H NMR (CDCl3) δ 8.35 (d, 1H), 8.21 (d, 1H), 7.35–7.16 (m, 6H), 7.04 (d, 1H), 6.64 (d, 1H), 5.20 (d, 1H), 4.60 (s, 2H), 4.37 (m, 1H), 2.09 (m, 2H), 1.82–1.48 (m, 6H); MS m/z 404 (M+1).

Workup

  1. stirringThe reaction mixture was stirred for an additional 30 minutes at −78° C
  2. customThe reaction mixture was quenched with water
  3. temperaturewarmed to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-779c4a32733a4aa2a40825f0dc583cf1
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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