Potassium Carbonate → 1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(thien-2-ylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde

HRID 379595Notes

Reaction equation

HRID 379595 reaction equation
Cl[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[CH:18]=[O:19].C(=O)([O-])[O-].[K+].[K+].[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[SH:31]>CC(C)=O>[CH3:12][N:8]1[C:9](=[O:11])[C:10]2[C:2]([S:31][C:27]3[S:26][CH:30]=[CH:29][CH:28]=3)=[C:3]([CH:18]=[O:19])[S:4][C:5]=2[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]1=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5226742-ThiophenethiolHCID 183666245-Chloro-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehyde

Product 1

HCID 183665901,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(thien-2-ylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-chloro-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehyde in acetone (30 ml) was added potassium carbonate (0.402 g) followed by 2-thiophene thiol (0.337 g). The reaction was stirred for 24 hours under nitrogen. The acetone was evaporated and the resulting residue was partitioned between ethyl acetate and water (1:1, 50 ml in total). The aqueous phase was extracted twice with ethyl acetate (25 ml) The organic extracts were washed with brine, then dried over magnesium sulfate, filtered and evaporated to leave a brown oil. This oil was triturated with diethyl ether to give the subtitle compound as a pale brown solid (0.528 g).

Workup

  1. customThe acetone was evaporated
  2. customthe resulting residue was partitioned between ethyl acetate and water (1:1, 50 ml in total)
  3. extractionThe aqueous phase was extracted twice with ethyl acetate (25 ml) The organic extracts
  4. washwere washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a brown oil
  9. customThis oil was triturated with diethyl ether

Sources & evidence

ORD record
ord-1abd861ae7a4454e920711dcf3e83dc4
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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