HCID 58458903, compound → HCID 136163962, compound

HRID 390354Notes

Reaction equation

HRID 390354 reaction equation
C([O:8][C:9]1[C:10](=[O:32])[N:11]([CH3:31])[C:12]([O:28][CH2:29][CH3:30])=[N:13][C:14]=1[C:15]1[O:19][N:18]=[C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:16]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH2:29]([O:28][C:12]1[N:11]([CH3:31])[C:10](=[O:32])[C:9]([OH:8])=[C:14]([C:15]2[O:19][N:18]=[C:17]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[N:16]=2)[N:13]=1)[CH3:30]

Participants

3

Reactant 1

HCID 58458903HCID 58458903, compound

Product 1

HCID 136163962HCID 136163962, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A yellow solution of 5-(benzyloxy)-2-ethoxy-6-(3-(4-fluorobenzyl)-1,2,4-oxadiazol-5-yl)-3-methylpyrimidin-4(3H)-one (0.150 g, 0.3421 mmol) in TFA (5 mL) was stirred 6 h at room temperature. Then, the reaction mixture was concentrated and the resulting yellow solid was heated with 1:1 EtOH/H2O and filtered to afford the title compound (0.11 g, 97%) as pale yellow solid. 1HNMR (500 MHz, CDCl3) δ: 9.49 (1H, s), 7.30 (2H, dd, J=8.4, 5.4 Hz), 7.02 (2H, t, J=8.6 Hz), 4.52 (2H, q, J=7.0 Hz), 4.15 (2H, s), 3.49 (3H, s), 1.44 (3H, t, J=7.0 Hz). HRMS (M+H) calcd for C16H16N4O4F: 347.1156. found: 347.3845. Anal calcd for C16H15N4O4F: C, 55.49; H, 4.36; N, 16.17; F, 5.48. found: C, 55.14; H, 4.32; N, 15.66; F, 5.85.

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. temperaturethe resulting yellow solid was heated with 1:1 EtOH/H2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9135babb5c564e67b1ecd49224f7e94f
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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