Hexachloroethane → 5-chloro-1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1423007Notes

Reaction equation

HRID 1423007 reaction equation
[CH2:1]([N:5]1[C:10]2=[C:11]([CH3:23])[N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=[C:9]2[C:8](=[O:24])[N:7]([CH3:25])[C:6]1=[O:26])[CH:2]([CH3:4])[CH3:3].[Cl:27]C(Cl)(Cl)C(Cl)(Cl)Cl.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:27][C:13]1[N:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:11]([CH3:23])=[C:10]2[C:9]=1[C:8](=[O:24])[N:7]([CH3:25])[C:6](=[O:26])[N:5]2[CH2:1][CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 674155471-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 686249505-chloro-1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (103 mg, 0.29 mmol) and hexachloroethane (400 mg, 1.7 mmol) are dissolved in anhydrous THF, and then 1.0M LiHMDS in THF (1.4 mL, 1.4 mmol) is added dropwise. The reaction mixture is stirred at room temperature for an hour, and then quenched with saturated ammonium chloride aqueous solution. The mixture is purified by silica-gel column chromatography to give pure product as off-white solids (yield: 64%). MS (ESI) m/z 390.2 [M+H]+.

Workup

  1. customquenched with saturated ammonium chloride aqueous solution
  2. customThe mixture is purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-04b077cd34594169a461ffca6048338d
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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