Sodium Iodide → HCID 12004133, compound

HRID 971268Notes

Reaction equation

HRID 971268 reaction equation
Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:19][C:20]([F:30])([F:29])[O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.[I-].[Na+].C(#N)C.C(=O)(O)[O-].[Na+]>>[Cl:18][C:17]1[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:26][C:25]4[CH:27]=[CH:28][C:22]([O:21][C:20]([F:19])([F:29])[F:30])=[CH:23][CH:24]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 590214784-Chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 12004133HCID 12004133, compoundYield 59.6%

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (0.103 g, 0.000366 mol), 4-(trifluoromethoxy)aniline (0.0983 mL, 0.000733 mol) and sodium iodide (0.020 g, 0.00013 mol) in Acetonitrile (3 mL, 0.06 mol) was heated via microwave in a sealed tube at 180° C. for 15 minutes. After cooling to room temperature, the mixture was added to saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Concentrated to leave an oil. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%) to give 0.092 g of an off-white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentrated
  6. customto leave an oil
  7. customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%)

Sources & evidence

ORD record
ord-de601a28c97c43b087cbec88e2c12cf2
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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