Hydrochloric Acid → HCID 178518206, compound

HRID 487859Notes

Reaction equation

HRID 487859 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:10]1[C:11]([OH:17])=[N:12][CH:13]=[N:14][C:15]=1[OH:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[OH:17][C:11]1[C:10]([S:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:15]([OH:16])[N:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 178518199HCID 178518199, compound

Product 1

HCID 178518206HCID 178518206, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Benzylmercaptan (6 ml, 0.05 mole) was added to a stirred and heated (90°) suspension of 5-bromo-4,6-dihydroxypyrimidine (9.5 g, 0.05 mole) and potassium carbonate (7.5 g, 0.055 mole) in dimethylformamide (25 ml). The reaction mixture was stirred and heated at 95-105° C. under an atmosphere of dry nitrogen for 3.5 hours. The mixture was poured into ice cold water (400 ml) with vigorous stirring and then acidified to pH 1 with hydrochloric acid. After stirring for 0.5 hours the suspension was filtered and the solid which was collected was rinsed several times with n-hexane and diethyl ether. The remaining brown solid was air dried to give 4,6-dihydroxy-5-benzylthiopyrimidine (5.5 g 50%) PMR spectrum: (d6DMSO) 3.96 (S, 2h); 7.2 (bm, 5H); 8.11 (s, 1H); 12.2 (bs, 2H).

Workup

  1. temperatureheated
  2. stirringThe reaction mixture was stirred
  3. stirringwith vigorous stirring
  4. stirringAfter stirring for 0.5 hours the suspension
  5. filtrationwas filtered
  6. customthe solid which was collected
  7. washwas rinsed several times with n-hexane and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-1ff9aa9a03fc4db186bc4c0ec64a4e85
Source dataset
uspto-grants-1994_03
Patent number
US05298480

Reaction notes

Loading…