Acetyl chloride → HCID 136268161, compound

HRID 1409581Notes

Reaction equation

HRID 1409581 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([OH:15])=[C:7]([OH:16])[N:6]=1.[C:21](Cl)(=[O:23])[CH3:22].[NH4+].[Cl-]>C(Cl)Cl>[CH3:14][O:13][C:11]([C:9]1[N:10]=[C:5]([CH2:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[Br:1])[NH:6][C:7](=[O:16])[C:8]=1[O:15][C:21](=[O:23])[CH3:22])=[O:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 178499081HCID 178499081, compound

Product 1

HCID 136268161HCID 136268161, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask, methyl 2-(2-bromobenzyl)-5,6-dihydroxypyrimidine-4-carboxylate (300 mg, 885 μmol) was combined with DCM (10 ml) to give a brown suspension. Acetyl chloride (1M in DCM) (2.21 ml, 2.21 mmol) was added slowly at room temperature. The mixture was stirred for one hour and then poured onto aqueous saturated NH4Cl solution and extracted with DCM. The organic phase was washed with brine solution, dried (Na2SO4), and evaporated to dryness under reduced pressure. Chromatography (SiO2; DCM) provided the title product as a white solid (0.33 g; 97%). LCMS: m/z=381/383 (MH+).

Workup

  1. customto give a brown suspension
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-348d6041967e4111974032b3d273aaff
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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