5-(4-(benzyloxy)-3-fluorophenyl)-2-(cyclohexylmethyl)-3-methylpyrimidin-4(3H)-one → 2-(cyclohexylmethyl)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one

HRID 2241308Notes

Reaction equation

HRID 2241308 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:29])[N:17]([CH3:28])[C:18]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:19][CH:20]=2)=[CH:11][C:10]=1[F:30])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH:22]1([CH2:21][C:18]2[N:17]([CH3:28])[C:16](=[O:29])[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:30])[CH:11]=3)=[CH:20][N:19]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 1

HCID 685158505-(4-(benzyloxy)-3-fluorophenyl)-2-(cyclohexylmethyl)-3-methylpyrimidin-4(3H)-one

Product 1

HCID 685161592-(cyclohexylmethyl)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(4-(benzyloxy)-3-fluorophenyl)-2-(cyclohexylmethyl)-3-methylpyrimidin-4(3H)-one (0.046 g, 0.11 mmol) in TFA (2 mL) was stirred at 40° C. for 2.5 hours. The reaction mixture was cooled to room temperature and concentrated to dryness. The crude product was purified by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (0.026 g; 73%) as a white foamy solid. LRMS (APCI pos) m/e 317 (M+1).

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude product was purified by flash column chromatography
  3. washeluting with 20:1 CH2Cl2/MeOH
  4. customThe product was obtained (0.026 g; 73%) as a white foamy solid

Sources & evidence

ORD record
ord-13f0d475f8c845818818ef9df9cbec4a
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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