Methanol → HCID 53785557, compound

HRID 2269153Notes

Reaction equation

HRID 2269153 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][CH2:12][C:13]([OH:15])=[S:14])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)(Cl)=O.[CH3:27]O>C(Cl)(Cl)Cl>[CH3:27][O:15][C:13](=[S:14])[CH2:12][CH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:2]([NH2:1])[N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178508405HCID 178508405, compound

Product 1

HCID 53785557HCID 53785557, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 3-(6-amino-9-benzyl-2-purinyl) thiopropionic acid (100 mg, 0.30 mmol) suspended in 10 ml of chloroform was added thionylchloride (0.14 ml, 2 mmol). After refluxing under heating for 1 hour methanol was dropped to the mixture under ice cooling. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (1% methanol/chloroform) to give the subject compound (70 mg, yield 68%).

Workup

  1. temperatureAfter refluxing
  2. additionwas dropped to the mixture under ice cooling
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-ced25397ceeb4bb785d487e979859fc7
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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