Acetic Anhydride → N-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-2-yl]acetamide

HRID 3166Notes

Reaction equation

HRID 3166 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9](=[O:20])[N:8]([CH3:21])[C:6]=2[N:7]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:19])[C:12]=1[C:10]1[C:9](=[O:20])[N:8]([CH3:21])[C:6]2[N:7]=[C:2]([NH:1][C:22](=[O:24])[CH3:23])[N:3]=[CH:4][C:5]=2[CH:11]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 53278642-amino-6-(2,6-dichlorophenyl)-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 5327865N-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-2-yl]acetamide

Conditions

Temperature
25 °C

Procedure

A mixture of 64.2 mg (0.20 mmol) of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one (from Example 12) and 1 mL of acetic anhydride was heated to reflux. The resulting solution was maintained at reflux for 20 minutes and concentrated at atmospheric pressure to about 0.25 mL volume. The solution was cooled to 25° C. and diluted with diethyl ether (1 mL). The separated crystals were filtered and washed with diethyl ether to provide N-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl]acetamide, wt 44.0 mg; mp 258°-260° C.

Workup

  1. temperaturewas heated to reflux
  2. temperatureThe resulting solution was maintained
  3. temperatureat reflux for 20 minutes
  4. concentrationconcentrated at atmospheric pressure to about 0.25 mL volume
  5. additiondiluted with diethyl ether (1 mL)
  6. filtrationThe separated crystals were filtered
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-040121136d37435a8bcc1f1ef88ef22c
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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