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Ethanol → 4-(2,4-Diamino-6-pyrimidyl)benzoic Acid Hydrochloride

HRID 1061006
Notes
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Reaction equation

HRID 1061006 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[C:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([OH:12])=[O:11].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C>[ClH:1].[NH2:8][C:6]1[N:5]=[C:4]([NH2:9])[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 694814324-(2,4-Diamino-6-pyrimidyl)benzoic Acid HydrochlorideYield 54%

Reagents, catalysts & solvents 4

HCID 178419050
HCID 178419050, compound
Catalyst
HCID 962WaterSolvent2×
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

In toluene (9 ml), 6-chloro-2,4-diaminopyrimidine (434 mg) was dissolved, followed by the addition of 4-carboxyphenylboronic acid (667 mg), ethanol (2.5 ml), sodium carbonate (635 mg), water (3.0 ml) and bis(triphenylphosphine)palladium (II) dichloride (65 mg). The resulting mixture was heated under reflux for 24 hours under an argon gas atmosphere. Ethyl acetate and water were added to the reaction mixture. The water layer so separated was made acidic with 2N hydrochloric acid. The insoluble matter was collected by filtration, washed with water and tetrahydrofuran and then dried, whereby the title compound (371 mg, 54%) was obtained.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 24 hours under an argon gas atmosphere
  3. customThe water layer so separated
  4. filtrationThe insoluble matter was collected by filtration
  5. washwashed with water and tetrahydrofuran
  6. customdried

Sources & evidence

ORD record
ord-58c75aa62f2d431eb6ca69d91e2a6904
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06525042B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes