Acetic Anhydride → 2-acetamido-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one

HRID 1025517Notes

Reaction equation

HRID 1025517 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(O)(=O)C>[C:20]([NH:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1361375922-Amino-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 1360008912-acetamido-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-amino-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one (2.0 g) in acetic anhydride (180 ml) and acetic acid (20 ml) was refluxed for 16 hours. The hot suspension was filtered and the filtrate was concentrated under reduced pressure until crystallization started. The precipitate was filtered off to give the pure title compound in 78% yield. The compound was characterized by its mass spectrum as follows: MS (m/z): 299 ([M+H]+, 100).

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe hot suspension was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure until crystallization
  4. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-7638cfebe31e4703a5e4cd0c223121e1
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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