Thionyl Chloride → 6-(chloromethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379600Notes

Reaction equation

HRID 379600 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[S:22][C:10]2[N:11]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:12](=[O:17])[N:13]([CH3:16])[C:14](=[O:15])[C:9]=2[C:8]=1[S:23][CH:24]([CH3:26])[CH3:25]>ClCCl>[Cl:3][CH2:6][C:7]1[S:22][C:10]2[N:11]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:12](=[O:17])[N:13]([CH3:16])[C:14](=[O:15])[C:9]=2[C:8]=1[S:23][CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 183665846-(hydroxymethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 183666156-(chloromethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (145 μl) was added to 6-(hydroxymethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.45 g) in dry dichloromethane (20 ml) and the mixture was stirred for 24 hours. The solvent was evaporated to give the subtitle compound as a an oil.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c7579460b23b4cb2b9bee22952e453e5
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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