Potassium Iodide → HCID 9864078, compound

HRID 379570Notes

Reaction equation

HRID 379570 reaction equation
[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][CH:10]=1.Cl[CH2:19][C:20]1[S:35][C:23]2[N:24]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:22]=2[CH:21]=1>CN(C)C=O.C(OCC)(=O)C>[N:9]1([CH2:19][C:20]2[S:35][C:23]3[N:24]([CH2:31][CH:32]([CH3:33])[CH3:34])[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:22]=3[CH:21]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 18366575HCID 18366575, compound

Product 1

HCID 9864078HCID 9864078, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium iodide (few crystals), potassium carbonate (140 mg) and benzimidazole (100 mg) were added to a solution of 6-chloromethyl-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (170 mg) in dimethylformamide (5 ml). After 2 h the reaction mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate solution thrice and with brine, then dried over magnesium sulfate and evaporated. Column chromatography of the residue eluting with isohexane:ethyl acetate (1:1 to 0:1) containing 1% Et3N gave the title compound (130 mg).

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution thrice and with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. washColumn chromatography of the residue eluting with isohexane:ethyl acetate (1:1 to 0:1)
  5. additioncontaining 1% Et3N

Sources & evidence

ORD record
ord-1850d9db48804295b769999efd506797
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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