Thionyl Chloride → 3-Benzyl-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 1465987Notes

Reaction equation

HRID 1465987 reaction equation
S(Cl)(Cl)=O.[CH2:5]([C:12]1[N:13]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)[N:14]=[C:15]2[C:20]=1[C:19](=[O:21])[N:18]([CH3:22])[C:17](=[N:23][C:24]([CH3:28])([CH3:27])[CH2:25]O)[NH:16]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:5]([C:12]1[N:13]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:32][CH:31]=2)[N:14]=[C:15]2[N:16]3[CH2:25][C:24]([CH3:28])([CH3:27])[N:23]=[C:17]3[N:18]([CH3:22])[C:19](=[O:21])[C:20]=12)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178481268HCID 178481268, compound

Product 1

HCID 119885773-Benzyl-2-(biphenyl-4-ylmethyl)-7,8-dihydro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-oneYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2.0 M solution of thionyl chloride (25 μL, 0.050 mmol) in CH2Cl2 is added into a solution of 3-benzyl-2-(biphenyl-4-ylmethyl)-6-(1-hydroxy-2-methylpropan-2-ylimino)-5-methyl-6,7-dihydro-2H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (5.0 mg, 0.010 mmol) in methylene chloride (1 mL). The reaction mixture is stirred at r.t. overnight, and then quenched with 5% NaHCO3. The resulting mixture is purified by chromatography to give 3.2 mg of the final product (Yield: 67%). MS (FAB) m/z 476.4 [M+H]+.

Workup

  1. customquenched with 5% NaHCO3
  2. customThe resulting mixture is purified by chromatography

Sources & evidence

ORD record
ord-f5b5e81c386449d88f3810bedb8acd0e
Source dataset
uspto-grants-2015_04
Patent number
US09000001B2

Reaction notes

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