Potassium Carbonate → 4-chloro-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one

HRID 2237631Notes

Reaction equation

HRID 2237631 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([N:10]([CH2:18][CH2:19][OH:20])[C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:9])[N:10]([C:11]3[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=3)[CH2:18][CH2:19][O:20][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 593025124,6-dichloro-N-(2-hydroxyethyl)-N-(4-iodophenyl)pyrimidine-5-carboxamide

Product 1

HCID 593025014-chloro-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred slurry of 4,6-dichloro-N-(2-hydroxyethyl)-N-(4-iodophenyl)pyrimidine-5-carboxamide (543 mg, 1.24 mmol) and potassium carbonate (350 mg, 2.53 mmol) in DMF was heated at 80° C. for 2 hours. The reaction was cooled, filtered, solids washed with small portion of DMF and the combined filtrates were concentrated in vacuo. The residue was chromatographed (40 g of silica gel, 0-70% EtOAc:heptane) to afford 4-chloro-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one as a white solid, 427 mg. 1H NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 7.80 (d, 2H), 7.17 (d, 2H), 4.77 (m, 2H), 4.03 (m, 2H). m/z=402.0 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washsolids washed with small portion of DMF
  4. concentrationthe combined filtrates were concentrated in vacuo
  5. customThe residue was chromatographed (40 g of silica gel, 0-70% EtOAc:heptane)

Sources & evidence

ORD record
ord-2c3f049830904c7686ed42208b3aa39f
Source dataset
uspto-grants-2010_05
Patent number
US07718645B2

Reaction notes

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