Sodium Hydroxide → N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 1163732Notes

Reaction equation

HRID 1163732 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27]C)=[O:26])[CH:20]=3)[C:15]([F:29])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([OH:27])=[O:26])[CH:20]=3)[C:15]([F:29])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22060860N2,N4-bis(3-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine

Product 1

HCID 10126258N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamineYield 58.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N2,N4-bis(3-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine (100 mg, 0.25 mmol) and NaOH (140 mg, 3.5 mmol) in THF:H2O (5 mL, each) was stirred at room temperature overnight. The reaction mixture was diluted with water (60 mL) and ethyl acetate (60 mL). The aqueous layer was separated, acidified with 1N HCl solution to pH 3. The formed precipitate was collected by filtration and recrystallized from methanol to give N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine (54 mg, 58%) as a white solid. 1H NMR (CD3OD): δ 7.31 (t, J=8.1 Hz, 1H), 7.42 (t, J=8.1 Hz, 1H), 7.61 (dm, J=7.8 Hz, 1H), 7.76 (dm, J=8.4 Hz, 1H), 7.89 (dm, J=7.2 Hz, 1H), 7.98 (d, J=3.6 Hz, 1H), 8.01 (m, 1H), 8.20 (m, 1H), 8.37 (m, 1H); LCMS: ret. time: 15.77 min.; purity: 98.84%; MS (m/e): 369.03 (MH+).

Workup

  1. customThe aqueous layer was separated
  2. filtrationThe formed precipitate was collected by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3b558c9f791343b69b92e7af1e9d26d1
Source dataset
uspto-grants-2010_10
Patent number
US07820819B2

Reaction notes

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