Oxalyl chloride → HCID 22484122, compound

HRID 2181358

Reaction equation

HRID 2181358 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:23]([OH:25])=O)=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[S:11][C:5]=2[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30].C(Cl)(=O)[C:32]([Cl:34])=O>ClCCl.CN(C)C=O>[Cl:34][CH2:32][C:23]([C:9]1[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]=2[S:11][C:10]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:21])([F:22])[F:20])=[O:25]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 52825261,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]thieno[2,3-d]pyrimidine-5-carboxylic acid

Product 1

HCID 22484122HCID 22484122, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-5-carboxylic acid, (prepared by the method of Example 8a) (3.665 g) was suspended in dichloromethane (70 ml) containing dimethyl formamide (1 drop) and treated with oxalyl chloride (1.47 ml). 1 hr after gas evolution ceased the reaction was concentrated in vacuo and stored under high vacuum for 1 h. The residue was redissolved in dichloromethane (50 ml) and treated with triethylamine (1 ml). To this solution was added trimethylsilyldiazomethane (7 mls of 2M solution in tetrahydrofuran) and the reaction was stirred at room temperature under an atmosphere of nitrogen for 4 hrs before HCl (8 ml, 4M in dioxane) was added. The reaction was stirred for 18 hrs before being concentrated in vacuo and the residue was purified by chromatography eluting with 2:1 isohexane:diethyl ether. The product was recrystallised from ethyl acetate and isohexane to yield the subtitle compound as white needles(4.616 g)

Workup

  1. custom1 hr
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane (50 ml)
  4. additiontreated with triethylamine (1 ml)
  5. additionTo this solution was added trimethylsilyldiazomethane (7 mls of 2M solution in tetrahydrofuran)
  6. additionwas added
  7. stirringThe reaction was stirred for 18 hrs
  8. concentrationbefore being concentrated in vacuo
  9. customthe residue was purified by chromatography
  10. washeluting with 2:1 isohexane
  11. customThe product was recrystallised from ethyl acetate and isohexane

Sources & evidence

ORD record
ord-e878c66bce344e8f8aa5136746291c0c
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Linked notes

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