Thionyl Chloride → 2-(Biphenyl-4-ylmethyl)-7,8-dihydro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one

HRID 2389523Notes

Reaction equation

HRID 2389523 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([N:11]=[C:12]([NH:19][C:20]([CH3:24])([CH3:23])[CH2:21]O)[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O>C(Cl)Cl>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:14](=[O:17])[N:13]([CH3:18])[C:12]4[N:11]([CH2:24][C:20]([CH3:23])([CH3:21])[N:19]=4)[C:10]3=[N:9]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 691966222-(Biphenyl-4-ylmethyl)-6-(1-hydroxy-2-methylpropan-2-ylamino)-5-methyl-2H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 119737392-(Biphenyl-4-ylmethyl)-7,8-dihydro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(biphenyl-4-ylmethyl)-6-(1-hydroxy-2-methylpropan-2-ylamino)-5-methyl-2H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (17 mg, 0.042 mmol) in methylene chloride (1 mL), is added 2.0 M CH2Cl2 solution of thionyl chloride (63 μL, 0.126 mmol) under argon. The reaction mixture is stirred at r.t. overnight. The reaction is quenched with 5% NaHCO3, and the resulting mixture is purified by chromatography to give 11 mg of the final product as white solids (Yield: 68%). 1H NMR (400 MHz, DMSO-d6+CDCl3) δ 1.36 (s, 6H), 3.30 (s, 3H), 3.69 (s, 2H), 5.30 (s, 2H), 7.36 (m, 3H), 7.43 (m, 2H), 7.58 (m, 4H), 8.10 (s, 1H). MS (FAB) m/z 386.1 [M+H]+.

Workup

  1. customThe reaction is quenched with 5% NaHCO3
  2. customthe resulting mixture is purified by chromatography

Sources & evidence

ORD record
ord-22eb5ad55d31427486ce86ada59d44c3
Source dataset
uspto-grants-2012_09
Patent number
US08273750B2

Reaction notes

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