Hydrochloric Acid → N2-(3-carboxymethyleneaminophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 1483522Notes

Reaction equation

HRID 1483522 reaction equation
C([O:3][C:4]([CH:6]=[N:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][CH2:30][O:31][C:24]=4[CH:23]=3)[C:18]([F:32])=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1)=[O:5])C.[Li+].[OH-].Cl>CO.O>[C:4]([CH:6]=[N:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][CH2:30][O:31][C:24]=4[CH:23]=3)[C:18]([F:32])=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22060312HCID 22060312, compound

Product 1

HCID 22061116N2-(3-carboxymethyleneaminophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The reaction of N2-(3-ethoxycarbonylmethyleneaminophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine (0.1 g) and LiOH (10 equivalents) in MeOH:water (1:1, v/v) for 1 h at room temperature followed by treatment with aqueous HCl gave the solid. The resulting solid was filtered, washed with water and dried to give N2-(3-carboxymethyleneaminophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 18.23 min.; purity: 87.6%; MS (m/e): 412.01 (MH+).

Workup

  1. customgave the solid
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8b098be87cea4291a6db390d16e4527c
Source dataset
uspto-grants-2016_08
Patent number
US09416112B2

Reaction notes

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