Acetyl chloride → HCID 178474657, compound

HRID 1504086Notes

Reaction equation

HRID 1504086 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[S:13][C:7]2[N:8]=[CH:9][N:10]=[C:11]([OH:12])[C:6]=2[CH:5]=1.[C:14](Cl)(=[O:16])[CH3:15]>ClCCl>[OH:12][C:11]1[C:6]2[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:14](=[O:16])[CH3:15])[S:13][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178510738HCID 178510738, compound

Product 1

HCID 178474657HCID 178474657, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen was added a solution of 6-(2-aminoethyl)thieno[2,3-d]pyrimidin-4-ol (570 mg, 2.92 mmol, 1.00 equiv) in 10 mL of dichloromethane. TEA (1.2 g, 11.86 mmol, 4.06 equiv) and acetyl chloride (460 mg, 5.86 mmol) were added at 0° C. under nitrogen. The resulting solution was stirred for 2 h at room temperature and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to give 400 mg (crude) of the desired N-(2-[4-hydroxythieno[2,3-d]pyrimidin-6-yl]ethyl)acetamide as a white solid. MS (ES): m/z 238 (M+H)+.

Workup

  1. customTo a 25-mL round-bottom flask (1 atm) purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-28d669604c9a480f8ae68dbeaaa42d78
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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