Potassium Carbonate → 6-bromo-9-(4-bromo-3,5-dimethyl-pyridin-2-yl methyl)-9H-purin-2-ylamine

HRID 722087Notes

Reaction equation

HRID 722087 reaction equation
[Br:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[Br:12][C:13]1[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([CH2:20]Cl)[C:14]=1[CH3:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:20][C:15]1[C:14]([CH3:22])=[C:13]([Br:12])[C:18]([CH3:19])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 167363514-Bromo-2-chloromethyl-3,5-dimethylpyridineHCID 1785082656-bromo-1H-purin-2-amine

Product 1

HCID 218830116-bromo-9-(4-bromo-3,5-dimethyl-pyridin-2-yl methyl)-9H-purin-2-ylamineYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-bromo-9H-purin-2-ylamine (2.4 g, 11 mmol), 4-bromo-2-chloromethyl-3,5-dimethyl pyridine (3.5 g, 15 mmol), K2CO3 (2.07 g, 15 mmol) and DMF (50 mL) was stirred at 50° C. for 2 h. Work-up and flash chromatography gave the title compound as a white solid (2.6 g, 56%). HPLC Rt: 5.415 min. 1H-NMR (CDCl3): δ 8.17 (s, 1H), 7.88 (s, 1H), 5.38 (s, 2H), 5.05 (s, 2H), 2.51 (s, 3H), 2.37 (s, 3H).

Sources & evidence

ORD record
ord-d0e91998d6a64901b97956fb345218ec
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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