Water → HCID 10040350, compound

HRID 859969Notes

Reaction equation

HRID 859969 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[N:7]=1.N12CCCN=C1CCCCC2.[I-].[NH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(#N)C>[CH2:3]([C:4]1[C:5]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[N:7]=2)=[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][N:28]2[N:27]=1)[CH:2]([CH3:14])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 694392334-(4-Methylpent-1-ynyl)-2-(methylthio)pyrimidine

Product 1

HCID 10040350HCID 10040350, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cold (0° C.) solution of 4-(4-methylpent-1-ynyl)-2-(methylthio)pyrimidine (2.5 g, 12 mmol) in acetonitrile (40 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (2.7 mL, 18 mmol) and 1-aminopyridinium iodide (3.49 g, 15.7 mmol). The resultant dark solution was allowed to warm to room temperature and stirred vigorously. The mixture was heated to 50° C. for 18 h then cooled to room temperature. Water was added and the mixture concentrated in vacuo. The residue was partitioned between water and ether. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed flash chromatography on silica gel (6:1 to 4:1 to 2:1 hexane-ethyl acetate) provided 2-isobutyl-3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine (2.0 g, 56%) as a yellow solid. 1H NMR (CDCl3) δ 8.51–8.48 (m, 2H), 8.36 (d, 1H), 7.35 (t, 1H), 7.19 (d, 1H), 6.91 (t, 1H), 3.04 (d, 2H), 2.68 (s, 3H), 2.20 (m, 1H), 1.03 (d, 6H); MS m/z 299 (M+1).

Workup

  1. temperatureThe mixture was heated to 50° C. for 18 h
  2. temperaturethen cooled to room temperature
  3. concentrationthe mixture concentrated in vacuo
  4. customThe residue was partitioned between water and ether
  5. washThe organic layer was washed with brine
  6. extractionThe aqueous layer was extracted with ether
  7. dry with materialthe combined organics were dried over magnesium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-8030430ff74e4f1c8d97a853534acc93
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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