Ethyl-oxido-oxo-sulfanylidene-lambda6-sulfane → 4-Chloro-5-methylthiothieno[2,3-d]pyrimidine

HRID 1678055

Reaction equation

HRID 1678055 reaction equation
Br[C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.C([Mg]Cl)(C)C.C[CH2:18][S:19](=S)([O-])=O>C1COCC1>[Cl:11][C:9]1[C:10]2[C:2]([S:19][CH3:18])=[CH:3][S:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 3633702Ethyl-oxido-oxo-sulfanylidene-lambda6-sulfaneHCID 454802995-Bromo-4-chlorothieno[2,3-d]pyrimidineHCID 178418918HCID 178418918, compound

Product 1

HCID 873505144-Chloro-5-methylthiothieno[2,3-d]pyrimidineYield 127.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5-bromo-4-chlorothieno[2,3-d]pyrimidine (750 mg, 3.0 mmol) was partially dissolved in anh. THF (8 mL), cooled to 0° C. and treated in portions with a 2M THF solution of i-PrMgCl (2.0 mL, 4.0 mmol). After 20 minutes, this solution was treated dropwise with methylmethanethiosulfonate (460 μl, 570 mg, 4.5 mmol). The cooling bath was removed and the mixture was stirred for 4 hours at 25° C. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic phase was washed with water, brine, dried (Na2SO4) and evaporated to give 830 mg crude product-ca 80 percent pure by GC. The material was purified by recrystallization from hot heptane to give 350 mg (45 percent) yield of tan crystals.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-35b841885da84ec48b95de1638c53f9d
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Linked notes

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