2-Methyl-2-thiopseudourea sulfate → 2-(Methylthio)-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine

HRID 602957Notes

Reaction equation

HRID 602957 reaction equation
CN([CH:4]=[C:5]1[CH2:9][N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][C:6]1=O)C.[O-]CC.[Na+].S(O)(O)(=O)=O.[CH3:39][S:40][C:41](=[NH:43])[NH2:42]>C(O)C>[CH3:39][S:40][C:41]1[N:42]=[CH:4][C:5]2[CH2:9][N:8]([C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][C:6]=2[N:43]=1

Participants

5

Reactant 3

HCID 752702-Methyl-2-thiopseudourea sulfate2×HCID 2723922Sodium ethoxide2×HCID 67065831HCID 67065831, compound

Product 1

HCID 670658712-(Methylthio)-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.83 g (12.63 mmol) of 4-[(dimethylamino)methylene]-1-tritylpyrrolidin-3-one in anhydrous ethanol (50 mL) was added sodium ethoxide (11.8 mL, 21% in ethanol). After stirring for 5 min, 3.51 g (25.25 mmol) of 2-methyl-2-thiopseudourea sulfate was aided and the reaction mixture heated at reflux temperature for 1 h. The mixture was cooled to ambient temperature and 3.51 g (25.25 mmol) of 2-methyl-2-thiopseudourea sulfate was added followed by 11.8 mL (21% in ethanol) of sodium ethoxide. The reaction mixture was refluxed for 1 h and cooled to ambient temperature. This process was repeated two additional times at which point the reaction mixture was evaporated in vacuo, diluted with 200 mL of a 1:1 mixture of ethyl acetate and saturated aqueous brine. The layers were separated and the aqueous phase extracted with three 100-mL portions of ethyl acetate. The combined organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was chromatographed on a Biotage® system (silica gel, 0 to 25% ethyl acetate/hexanes gradient) to yield the title compound as a white solid. LC/MS=410.3 (M+1).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux temperature for 1 h
  3. temperatureThe reaction mixture was refluxed for 1 h
  4. temperaturecooled to ambient temperature
  5. customwas evaporated in vacuo
  6. additiondiluted with 200 mL of a 1:1 mixture of ethyl acetate and saturated aqueous brine
  7. customThe layers were separated
  8. extractionthe aqueous phase extracted with three 100-mL portions of ethyl acetate
  9. dry with materialThe combined organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customThe resulting residue was chromatographed on a Biotage® system (silica gel, 0 to 25% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-6dae75ff16204fa08983f4560511c828
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Reaction notes

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