2,4-Dichloropyrimidine → N2,N4-bis(6-Hydroxy-3-quinolinyl)-2,4-pyrimidinediamine

HRID 495473Notes

Reaction equation

HRID 495473 reaction equation
Br.Br.[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([NH2:14])=[CH:7]2.Cl[C:16]1[N:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=1>CC(O)C>[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([NH:14][C:16]1[N:21]=[C:20]([NH:14][C:8]3[CH:9]=[N:10][C:11]4[C:6]([CH:7]=3)=[CH:5][C:4]([OH:3])=[CH:13][CH:12]=4)[CH:19]=[CH:18][N:17]=1)=[CH:7]2

Participants

4

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 223268146-Hydroxy-3-aminoquinoline di-hydrobromide

Product 1

HCID 20826886N2,N4-bis(6-Hydroxy-3-quinolinyl)-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 6-hydroxy-3-aminoquinoline di-hydrobromide (0.064 g, 0.2 mmol) and 2,4-dichloropyrimidine (0.148 g, 1 mmol) in IPA (1 mL) was heated at reflux overnight. The reaction was cooled to RT and a yellow solid was filtered off and washed with IPA. The solid was purified by flash chromatography in CH2Cl2/MeOH/NH4OH (90/10/1). The fractions containing the compound were combined and the solvents were removed under vacuum. The residue was purified by reverse-phase preparative HPLC (CH3CN/water/TFA) to give the bis-trifluoroacetate of the title compound as a yellow solid. MS (MH+)=397.2, Calc'd for: C22H16N6O2—396.4.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationa yellow solid was filtered off
  4. washwashed with IPA
  5. customThe solid was purified by flash chromatography in CH2Cl2/MeOH/NH4OH (90/10/1)
  6. additionThe fractions containing the compound
  7. customthe solvents were removed under vacuum
  8. customThe residue was purified by reverse-phase preparative HPLC (CH3CN/water/TFA)

Sources & evidence

ORD record
ord-0bef2f7dfbc0486d82ce477d0f12325e
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

Loading…