Carbon Dioxide → HCID 15540788, compound

HRID 1386444Notes

Reaction equation

HRID 1386444 reaction equation
[Li]CCCC.[O:6]([C:13]1[CH:18]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]=[C:15]([S:26][CH3:27])[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:28](=[O:30])=[O:29].Cl>C1COCC1>[O:6]([C:13]1[C:18]([C:28]([OH:30])=[O:29])=[C:17]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]=[C:15]([S:26][CH3:27])[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 15540787HCID 15540787, compoundHCID 178418339Butyllithium

Product 1

HCID 15540788HCID 15540788, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-BuLi (1.0M, 1.2 mmol) was added to a stirred solution of 4,6-diphenoxy-2-(methylthio)pyrimidine (298 mg, 1.0 mmol) in THF (2 ml) at −78° C. The reaction mixture was stirred for 2 hours and warmed up to 0° C. Dry ice (5 pieces) was added in small pieces over 10 minutes and the reaction was warmed to room temperature for 30 minutes. Dilute HCl was added and the mixture was extracted with EtOAc. The combined organic extract was dried over MgSO4, filtered and evaporated in vacuo to give a yellow solid that was recrystallized from ethyl acetate/hexanes to give a yellow solid (243 mg, 71% yield), m.p. 97-98° C.

Workup

  1. temperaturethe reaction was warmed to room temperature for 30 minutes
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe combined organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a yellow solid
  8. customthat was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-59bd4ce4a9734a799592ec0f85094f89
Source dataset
uspto-grants-2001_07
Patent number
US06265428B1

Reaction notes

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