Acetyl chloride → HCID 57636133, compound

HRID 216104Notes

Reaction equation

HRID 216104 reaction equation
[C:1](O)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.C(Cl)(=O)C>N1C=CC=CC=1>[CH3:19][O:18][C:16]1[N:17]=[C:12]([C:8]2[CH:7]=[C:6]([NH:5][C:1](=[O:3])[CH3:2])[CH:11]=[CH:10][CH:9]=2)[CH:13]=[C:14]([NH:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:15]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 69071157HCID 69071157, compound

Product 1

HCID 57636133HCID 57636133, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of [6-(3-amino-phenyl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine acetate [156 mg, 0.38 mmol, Example 2] in pyridine (1.3 mL) is added acetyl chloride (32 μL, 0.45 mmol). The reaction mixture is stirred for 3 hours at ambient temperature, quenched with the addition of water (20 mL), and extracted three times with EtOAc (20 mL). The combined extracts are washed four times with aqueous copper sulfate solution (10 mL), with water (10 mL), with brine (10 mL), dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The resulting solid is subjected to flash column chromatography on silica gel (4.5 g) eluting with 3% MeOH in DCM to afford N-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-acetamide [51 mg, 34%, Example 6(b)]. LCMS: RT=2.3 minutes, MS: 393 (M+H).

Workup

  1. customquenched with the addition of water (20 mL)
  2. extractionextracted three times with EtOAc (20 mL)
  3. washThe combined extracts are washed four times with aqueous copper sulfate solution (10 mL)
  4. dry with materialwith water (10 mL), with brine (10 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporator
  7. washeluting with 3% MeOH in DCM

Sources & evidence

ORD record
ord-bdbffc5d83b24b1db45d85d90ba67948
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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