Water → 3-chloro-5-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 57659

Reaction equation

HRID 57659 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:3]1=[O:30].[Cl:31]C(Cl)(Cl)C(Cl)(Cl)Cl.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.O>C(Cl)Cl.C1COCC1>[Cl:31][C:9]1[N:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)[N:11]=[C:5]2[C:6]=1[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]2[CH2:25][C:26]([CH3:27])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 700974725-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 700953303-chloro-5-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 92.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (500 mg, 1.24 mmol) and hexachloroethane (587 mg, 2.48 mmol) are dissolved in 8 mL of methylene chloride, and then 1.0 M LiHMDS (2.48 mL, 2.48 mmol) in THF is added dropwise. After the reaction mixture is stirred at room temperature for 10 min, 100 mL of deionized water is added, and then extracted with methylene chloride four times (30 mL×4). The combined organic phase is dried over anhydrous sodium sulfate. After filtration, the filtrate is evaporated to dryness to give 500 mg of crude product as brown solids, which is used in the next step without further purification. MS (ESI) m/z 438.2 [M+H]+.

Workup

  1. extractionextracted with methylene chloride four times (30 mL×4)
  2. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-4e697967616d4cdf8d5d6ee1edca4796
Source dataset
uspto-grants-2016_09
Patent number
US09434730B2

Linked notes

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