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

HRID 2195355Notes

Reaction equation

HRID 2195355 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-29dd5201cfa6467d8d2d668d2079df81
Source dataset
uspto-grants-2012_12
Patent number
US08334296B2

Reaction notes

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