Citric Acid → HCID 21089195, compound

HRID 350903Notes

Reaction equation

HRID 350903 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[C:8]([S:24][CH3:25])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([O:18]C)=[O:17])[C:10](=[O:12])[CH:11]=1.O1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[OH-].[Na+].O>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[C:8]([S:24][CH3:25])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([OH:18])=[O:17])[C:10](=[O:12])[CH:11]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 312751,4-DioxaneHCID 21090186methyl 3-[4-[(2,4-difluorobenzyl)oxy]-2-(methylthio)-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate

Product 1

HCID 21089195HCID 21089195, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of the ester (0.4 g, 0.0009 mol) obtained from step 3, in 2N NaOH (0.9 mL) and dioxane (0.5 mL) was stirred at room temperature for 1.5 h. The resulting clear solution was diluted with water (5.0 mL), acidified with 5% citric acid and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (2×15 mL), dried (Na2SO4), and concentrated to afford the title compound (0.38 g) as a white powder: 1H NMR (CD3OD/400 MHz) δ 8.06 (d, 1H, J=8.0 Hz), 7.81 (s, 1H), 7.51 (m, 2H), 6.99 (m 2H), 5.64 (s, 1H), 5.48 (s, 2H), 2.50 (s, 3H), and 2.15 (s, 3H); ES-HRMS m/z 419.0892(M+H calcd for C20H17N2O4SF2 requires 419.0872).

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (2×15 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-756ea5b5ad6b4c95a73d9cab8cfeb14c
Source dataset
uspto-grants-2007_02
Patent number
US07183287B2

Reaction notes

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