Acetic Anhydride → HCID 10098195, compound

HRID 750810Notes

Reaction equation

HRID 750810 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[O:5][C:6]1[N:11]=[C:10]([NH2:12])[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[N:7]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[O:5][C:6]1[N:11]=[C:10]([NH:12][C:32](=[O:34])[CH3:33])[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[N:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10073817HCID 10073817, compound

Product 1

HCID 10098195HCID 10098195, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a round bottom flask fitted with a magnetic stirrer bar and rubber septum was added 2-(3,4-difluorophenoxy)-4-amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Example 32) (20 mg, 0.04 mmol), 500 μL acetic anhydride and 10 mg of 4-(N,N-dimethylamino)pyridine (DMAP). The mixture was heated at reflux for 10 minutes and then worked up by removing the solvent/reagent under high vacuum. Flash chromatography on silica gel (70/30 hexanes/ethyl acetate) afforded the desired product. 1H-NMR 500 MHz (CDCl3): δ 2.41 (s, 3H), 7.06-7.67(m, 10H), 8.03 (bs, 1H).

Workup

  1. customTo a round bottom flask fitted with a magnetic stirrer bar
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 10 minutes
  4. customby removing the solvent/reagent under high vacuum

Sources & evidence

ORD record
ord-b76306ab68464ce8bd38bb773c00cb7a
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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