Butanal → 5-Bromo-N2-(4-butylamino-phenyl)-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine

HRID 1785329Notes

Reaction equation

HRID 1785329 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][C:18]3[NH:19][CH:20]=[N:21][CH:22]=3)[C:12]([Br:23])=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[CH:24](=O)[CH2:25][CH2:26][CH3:27].C([BH3-])#N.[Na+]>CO>[Br:23][C:12]1[C:13]([NH:15][CH2:16][CH2:17][C:18]2[NH:19][CH:20]=[N:21][CH:22]=2)=[N:14][C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 261ButanalHCID 5003444Sodium cyanoborohydrideHCID 57593472N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamine

Product 1

HCID 575936435-Bromo-N2-(4-butylamino-phenyl)-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamineYield 11.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (1 g, 2.6 mmole, prepared according to procedure 21) was dissolved in MeOH (10 ml), butanal (2.6 ml, 2.9 mmole) was added at room temperature and the reaction mixture was stirred at room temperature for 20 minutes. Sodium cyanoborohydride (266 mg, 3.6 mmole) was added and the reaction mixture was stirred at room temperature overnight. After extraction with ethylacetate/bicarbonate solution (3×) the combined organic layers were washed with saturated NaCl-solution, dried over magnesium sulfate and evaporated. The crude product was purified by flashmaster chromatography (dichloromethane:MeOH 95:5) to provide 5-Bromo-N2-(4-butylamino-phenyl)-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (130 mg). ESI-MS: 431.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionAfter extraction with ethylacetate/bicarbonate solution (3×) the combined organic layers
  3. washwere washed with saturated NaCl-solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude product was purified by flashmaster chromatography (dichloromethane:MeOH 95:5)

Sources & evidence

ORD record
ord-42efd63911934d84afb4ce4a8c2b54cc
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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