HCID 14460145, compound → HCID 178440000, compound

HRID 1590078Notes

Reaction equation

HRID 1590078 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([C:24](OCC)=[O:25])=[C:22]([CH:29]([CH3:31])[CH3:30])[N:21]=[C:20]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:19]=2)=[CH:14][CH:13]=1>O1CCCC1.CCCCCC>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]2[C:23](=[CH:24][OH:25])[C:22]([CH:29]([CH3:31])[CH3:30])=[N:21][C:20]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[N:19]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14460145HCID 14460145, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178440000HCID 178440000, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Diisobutylaluminum hydride (DIBAL-H) (1M in tetrahydrofuran (THF) (55 ml, 55 mmol) was added dropwise to a 0° C. solution of 4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-ethoxycarbonyl-pyrimidine obtained in step (ii) above (4.000 gm, 11 mmol) in THF (50 ml). The solution was then allowed to warm to room temperature and the mixture stirred for 3 hours. The solution was then cooled to 0° C. and quenched with saturated NH4Cl (55 ml). The solution was diluted with ether (100 ml) and the mixture was filtered through a celite pad and washed with ether. The filtrate was entirely organic and was dried over MgSO4, filtered and concentrated to give a yellow oil. The oil was dissolved in hot hexane and cooled to afford the title compound as a white solid (2.686 gm, 76%) (mp 183°-184° C.).

Workup

  1. temperatureThe solution was then cooled to 0° C.
  2. customquenched with saturated NH4Cl (55 ml)
  3. additionThe solution was diluted with ether (100 ml)
  4. filtrationthe mixture was filtered through a celite pad
  5. washwashed with ether
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow oil
  10. temperaturecooled

Sources & evidence

ORD record
ord-427622bfb0c24fb982b702ae3af4ede3
Source dataset
uspto-grants-1993_04
Patent number
US05202327

Reaction notes

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