o-Fluorobenzaldehyde → 5-[(2-Fluorophenyl)hydroxymethyl]-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 2181362Notes

Reaction equation

HRID 2181362 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].CC[Mg+].[Br-].[F:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=[O:37]>O1CCCC1>[F:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]([OH:37])[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

5

Reactant 3

HCID 67970o-FluorobenzaldehydeHCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 178461630HCID 178461630, compound

Product 1

HCID 102081985-[(2-Fluorophenyl)hydroxymethyl]-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (Example 1 part c)) (100 mg) was dissolved in tetrahydrofuran (2 mls) and EtMgBr (250 ul of 1M solution in tetrahydrofuran) was added. After 10 mins 2-fluorobenzaldehyde (250 ul of a 1M solution in tetrahydrofuran) was added. After 1 hr the reaction was quenched via addition of water. The reaction was concentrated in vacuo and extracted into dichloromethane, concentrated in vacuo and the residue purified via chromatography eluting with 0-100% diethyl ether in isohexane to yield the title compound (9 mg).

Workup

  1. customAfter 1 hr the reaction was quenched via addition of water
  2. concentrationThe reaction was concentrated in vacuo
  3. extractionextracted into dichloromethane
  4. concentrationconcentrated in vacuo
  5. customthe residue purified via chromatography
  6. washeluting with 0-100% diethyl ether in isohexane

Sources & evidence

ORD record
ord-ac6ac927da5d401da9947cd15fe23a8b
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Reaction notes

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