Phenol → HCID 11584042, compound

HRID 1455755Notes

Reaction equation

HRID 1455755 reaction equation
Cl[C:2]1[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH3:21])[N:5]=[C:4]([C:22]2[C:27]([CH2:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:30][CH3:31])[N:3]=1.[C:32]1([OH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC([O-])(C)C.[K+].C([O-])(O)=O.[Na+]>CCOC(C)=O.CC(O)(C)C.CC(N(C)C)=O>[CH2:30]([C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([CH2:28][CH3:29])[C:22]=1[C:4]1[N:5]=[C:6]([CH3:21])[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:2]([O:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:3]=1)[CH3:31]

Participants

8

Reactant 4

HCID 996PhenolHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 57531455HCID 57531455, compound

Product 1

HCID 11584042HCID 11584042, compound

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent3×

Conditions

Temperature
70 °C

Procedure

To a vial containing [4-chloro-2-(2,6-diethyl-phenyl)-6-methyl-pyrimidin-5-ylmethyl]-methyl-(1S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine 9 (0.1 mL of a 0.2 M DMA solution, 0.02 mmol) is added phenol (0.1 mL of a 0.3 M DMA solution, 0.03 mmol) and KOtBu (0.1 mL of a 0.3 M solution in 7:3 DMA:tBuOH, 0.03 mmol) and allowed to stir at 70° C. for 16 h. EtOAc (50 mL) and sat. NaHCO3 (50 mL) are then added and the organic layer is washed with water (100 mL), brine (100 mL) and dried over Na2SO4. The crude solution is filtered, concentrated and purified by SiO2 flash chromatography using hexanes:Et2O (5:1) affording (1S)-N-{[2-(2,6-diethylphenyl)-4-methyl-6-phenoxypyrimidin-5-yl]methyl}-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine as a colorless oil. [mass expected (491.67); mass found (491.42)].

Workup

  1. washthe organic layer is washed with water (100 mL), brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationThe crude solution is filtered
  4. concentrationconcentrated
  5. custompurified by SiO2 flash chromatography

Sources & evidence

ORD record
ord-061c095a76f6487e954ae3fe9f5fdf00
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

Loading…