Acetic Anhydride → HCID 18332708, compound

HRID 2269152Notes

Reaction equation

HRID 2269152 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH2:13][NH2:14])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30]>ClCCl.[Cl-].[Na+].O>[C:29]([NH:14][CH2:13][CH2:12][S:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:2]([NH2:1])[N:10]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 183327256-Amino-9-benzyl-2-(2-aminoethyl)thiopurine

Product 1

HCID 18332708HCID 18332708, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 6-amino-9-benzyl-2-(2-aminoethyl)thiopurine (50 mg, 0.17 mmol) suspended in 2 ml of dichloromethane was added triethylamine (30 ml, 0.2 mmol) and then acetic acid anhydride (20 ml, 0.2 mmol) under ice cooling. After 1 hour the mixture warmed to room temperature. Thereto was added saturated brine. The mixture was extracted with chloroform and the organic layer was dried on magnesium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (34 mg, yield 66%).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. customthe organic layer was dried on magnesium sulfate
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue was purified with silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-e96699ba38fd40dba244700a4c591488
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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