2-Methyl-3-buten-2-ol → 5-[3-Hydroxy-3-methyl-1-butenyl]-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 2181351Notes

Reaction equation

HRID 2181351 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26].[CH3:29][C:30]([OH:34])([CH:32]=[CH2:33])[CH3:31]>>[OH:34][C:30]([CH3:31])([CH3:29])[CH:32]=[CH:33][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26]

Participants

3

Reactant 2

HCID 82572-Methyl-3-buten-2-olHCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 697466215-[3-Hydroxy-3-methyl-1-butenyl]-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Procedure

Prepared using 5-bromo-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione and 2-methyl-3-buten-2-ol. The crude product was purified by flash silica chromatography eluting with a gradient of 0-2% ethanol in dichloromethane to give the title compound as a cream foam (0.20 g).

Workup

  1. customPrepared
  2. customThe crude product was purified by flash silica chromatography
  3. washeluting with a gradient of 0-2% ethanol in dichloromethane

Sources & evidence

ORD record
ord-96ee60cbe7ac41d49640a0f0fe1b1e34
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Reaction notes

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