Dimethylformamide → HCID 22258007, compound

HRID 1611047Notes

Reaction equation

HRID 1611047 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([C:25]([OH:27])=O)=[C:16]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:17][C:11]=2[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:9]1=[O:32].[CH3:33][N:34](C)[CH:35]=O>ClCCl>[CH3:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([C:25]([N:34]([CH3:35])[CH3:33])=[O:27])=[C:16]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:17][C:11]=2[N:10]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:9]1=[O:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 22257958HCID 22257958, compound

Product 1

HCID 22258007HCID 22258007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.087 ml) was added to a stirred solution of 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-6-phenylmethyl-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid (0.37 g) and dimethylformamide (0.01 ml) in anhydrous dichloromethane (20 ml). After 1 hour, the solution was evaporated. The residue was dissolved in anhydrous tetrahydrofuran (7 ml) and 1 ml of this solution was added to a stirred mixture of 40% aqueous dimethylamine solution (1 ml) and saturated sodium hydrogen carbonate solution (2 ml). After 30 minutes water (10 ml) was added and the mixture was extracted with ethyl acetate (10 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was recrystallised from ethyl acetate/isohexane to give the title compound (0.025 g).

Workup

  1. customthe solution was evaporated
  2. dissolutionThe residue was dissolved in anhydrous tetrahydrofuran (7 ml)
  3. addition1 ml of this solution was added to a stirred mixture of 40% aqueous dimethylamine solution (1 ml) and saturated sodium hydrogen carbonate solution (2 ml)
  4. additionAfter 30 minutes water (10 ml) was added
  5. extractionthe mixture was extracted with ethyl acetate (10 ml)
  6. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was recrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-b760b308acd9496a9f3068b9406ebf2f
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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