Citric Acid → HCID 70981500, compound

HRID 2280718Notes

Reaction equation

HRID 2280718 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][N:13]=[C:12]([S:21][CH3:22])[N:11]=2)[CH2:4]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][N:13]=[C:12]([S:21][CH3:22])[N:11]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 71237152HCID 71237152, compound

Product 1

HCID 70981500HCID 70981500, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of ethyl 4-((1R,3S)-3-methoxycyclohexylamino)-2-(methylthio)pyrimidine-5-carboxylate (1.4284 g, 4.39 mmol) in ethanol (12.54 mL) was added aqueous sodium hydroxide solution (1 N, 8.78 mL, 8.78 mmol) and the mixture was stirred for 2 h. The reaction was concentrated, diluted with water (50 mL), and then neutralized while stirring with aqueous citric acid solution (2 M, 5.49 mL, 10.97 mmol). The precipitate was filtered, then washed with water (2×50 mL) and dried to afford 4-((1R,3S)-3-methoxycyclohexylamino)-2-(methylthio)pyrimidine-5-carboxylic acid (1.1679 g, 3.93 mmol, 89% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.22 (s, 1H), 8.65 (d, J=7.03 Hz, 1H), 8.51 (s, 1H), 4.07-4.24 (m, 1H), 3.29-3.33 (m, 1H), 3.26 (s, 3H), 2.46 (s, 3H), 2.15 (d, J=12.10 Hz, 1H), 1.63-1.88. (m, 3H), 1.21-1.48 (m, 4H); MS (ESI) m/z 298.1 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water (50 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with water (2×50 mL)
  5. customdried

Sources & evidence

ORD record
ord-0f9f62192ea3444ab0d0376a6eb42f10
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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