5-(4-(benzyloxy)-3-fluorophenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one → 5-(3-fluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

HRID 1676336Notes

Reaction equation

HRID 1676336 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]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH: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>[F:30][C:10]1[CH:11]=[C:12]([C:15]2[C:16](=[O:29])[N:17]([CH3:28])[C:18]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:19][CH:20]=2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

3

Reactant 1

HCID 673485585-(4-(benzyloxy)-3-fluorophenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Product 1

HCID 673501215-(3-fluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(4-(benzyloxy)-3-fluorophenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.133 g, 0.331 mmol) in TFA (1.5 mL) was stirred at 40° C. for 3.5 hours. The reaction mixture was concentrated to dryness and then purified by flash column chromatography, eluting with 20:1 dichloromethane/MeOH. The desired product (0.103 g, 100%) was obtained as a foamy white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.81 (br s, 1H), 8.96 (br s, 1H), 7.86 (s, 1H), 7.56-7.45 (m, 3H), 7.37 (t, J=7.4 Hz, 2H), 7.27 (m, 1H), 7.15 (t, J=7.2 Hz, 1H), 6.92 (t, J=9.0 Hz, 1H), 3.54 (s, 3H). LRMS (APCI pos) m/e 312 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by flash column chromatography
  3. washeluting with 20:1 dichloromethane/MeOH

Sources & evidence

ORD record
ord-0dbfd98a5b6241f78c318a50cb062a1b
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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