6-(4-(benzyloxy)-3-fluorophenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one → 6-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1676392Notes

Reaction equation

HRID 1676392 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20](=[O:21])[N:19]3[CH2:22][CH2:23][N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]3=[N:17][CH:16]=2)=[CH:11][C:10]=1[F:31])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[F:31][C:10]1[CH:11]=[C:12]([C:15]2[C:20](=[O:21])[N:19]3[CH2:22][CH2:23][N:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:18]3=[N:17][CH:16]=2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

3

Reactant 1

HCID 673466776-(4-(benzyloxy)-3-fluorophenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Product 1

HCID 673463376-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-(4-(benzyloxy)-3-fluorophenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (0.084 g, 0.20 mmol) in TFA (2 mL) was stirred at 40° C. for 3 hours. The reaction was concentrated to dryness and then dried under vacuum to yield a crude residue that was purified by flash column chromatography, eluting with 25:1 CH2Cl2/MeOH. The product was obtained (80 mg; 94%) as a white solid as a TFA salt. 1H-NMR (400 MHz, DMSO-d6) δ 9.89 (br s, 1H), 7.98 (s, 1H), 7.82 (m, 2H), 7.52 (dd, 1H), 7.42 (m, 2H), 7.32 (m, 1H), 7.14 (m, 1H), 6.95 (m, 1H), 4.19 (m, 4H). LRMS (APCI pos) m/e 324 (M+1).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customdried under vacuum
  3. customto yield a crude residue that
  4. customwas purified by flash column chromatography
  5. washeluting with 25:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-393799bcbefb4dd08df67d9514dec935
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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