Acetonitrile → HCID 12004127, compound

HRID 971261Notes

Reaction equation

HRID 971261 reaction equation
Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27].C(#N)C.I.[Na]>>[F:19][C:18]([F:21])([F:20])[C:16]1[CH:15]=[CH:14][N:13]=[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:27][C:26]4[CH:28]=[CH:29][CH:30]=[C:24]([O:23][CH3:22])[CH:25]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)[CH:17]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 108243-MethoxyanilineHCID 24841Hydrogen iodideHCID 5360545SodiumHCID 59021489HCID 59021489, compound

Product 1

HCID 12004127HCID 12004127, compoundYield 24.9%

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chloro-7-(4-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (0.041 g, 0.00013 mol), 3-methoxyaniline (0.018 mL, 0.00016 mol) in acetonitrile (1.00 mL, 0.0191 mol) and 47% HI (0.11 mL, 0.001 mol) was heated at 160° C. for 10 minutes in in a sealed tube via microwave. After cooling to r.t., the mixture was poured into saturated aqueous sodium bicarbanate (5 mL) and extracted with ethyl acetate (10 mL). The organic layer was washed with brine and dried over magnesium sulfate. Concentrated to leave a brown solid. Residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%) to give a white foam (0.013 g)

Workup

  1. temperatureAfter cooling to r.t.
  2. extractionextracted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentrated
  6. customto leave a brown solid
  7. customResidue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%)

Sources & evidence

ORD record
ord-4aaeabc375074383bbd0fdfac2aa5088
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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