Water → HCID 21478860, compound

HRID 2292568Notes

Reaction equation

HRID 2292568 reaction equation
C(=O)([O-])[O-].[K+].[K+].[SH:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1.Br[CH2:15][CH2:16][CH:17]1[O:21][CH2:20][CH2:19][O:18]1.O>CC(C)=O>[O:18]1[CH2:19][CH2:20][O:21][CH:17]1[CH2:16][CH2:15][S:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 178418793HCID 178418793, compound

Product 1

HCID 21478860HCID 21478860, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (0.766 g) was added to a stirred solution of 2-mercaptopyrimidine (0.622 g) in acetone (10 cm3) at ambient temperature. 2-(2-Bromoethyl)-1,3-dioxolane (1 g) was added to the resulting mixture and the reaction heated under reflux for 3.5 hours. The reaction mixture was left to cool overnight, then poured into water and extracted with diethyl ether. The organic phase was dried with magnesium sulfate and evaporated under reduced pressure to give a yellow oil. This material was used in step 2 without further purification. M+ =212; 1H NMR (CDCl3): δ2.25 (2H,m); 3.25(2H,t); 3.90 (2H,m); 4.00 (2H,m); 5.05 (1H,t); 6.96 (1H,t); 8.52 (2H,d).

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 3.5 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool overnight
  5. extractionextracted with diethyl ether
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto give a yellow oil
  9. customThis material was used in step 2 without further purification

Sources & evidence

ORD record
ord-b3b527894791415a968ab6fa56817f07
Source dataset
uspto-grants-1997_11
Patent number
US05684011

Reaction notes

Loading…