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

HRID 1676384Notes

Reaction equation

HRID 1676384 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[C:19]([F:31])[CH:18]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[CH2:1]([NH:8][C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:31])[CH:18]=2)=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 673481582-(benzylamino)-5-(4-(benzyloxy)-3-fluorophenyl)-3-methylpyrimidin-4(3H)-one

Product 1

HCID 673462122-(benzylamino)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(benzylamino)-5-(4-(benzyloxy)-3-fluorophenyl)-3-methylpyrimidin-4(3H)-one (0.145 g, 0.349 mmol) in TFA (4 mL) was stirred at 40° C. for 5 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 20:1 CH2Cl2/MeOH. The product was obtained (105 mg; 93%) as a white foam solid. 1H NMR (400 MHz, DMSO-d6) δ 9.74 (br s, 1H), 7.93 (br s, 1H), 7.84 (s, 1H), 7.45 (m, 1H), 7.38-7.29 (m, 4H), 7.27-7.20 (m, 2H), 6.89 (t, 1H), 4.62 (d, 2H), 3.41 (s, 3H). LRMS (APCI pos) m/e 326 (M+1).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customdried under vacuum

Sources & evidence

ORD record
ord-5f48bbd4afee4665ae3efd925892c80e
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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