2,6-Bis(bromomethyl)pyridine → 3-(6-Bromomethylpyridin-2-ylmethyl)-7-(5-methyl-2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine

HRID 876988Notes

Reaction equation

HRID 876988 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[C:8]3[NH:16][N:15]=[N:14][C:9]=3[N:10]=[C:11]([NH2:13])[N:12]=2)=[CH:4][CH:3]=1.[Br:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25]Br)[N:20]=1>CCCCCC.CCOC(C)=O>[Br:17][CH2:18][C:19]1[N:20]=[C:21]([CH2:25][N:14]2[C:9]3[N:10]=[C:11]([NH2:13])[N:12]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[CH:3][CH:4]=4)[C:8]=3[N:16]=[N:15]2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6036102,6-Bis(bromomethyl)pyridineHCID 178423995HCID 178423995, compound

Product 1

HCID 667183513-(6-Bromomethylpyridin-2-ylmethyl)-7-(5-methyl-2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Prepared from 7-(5-methyl-2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine and 2,6-bis(bromomethyl)pyridine by the alkylation method described in Example 36; NMR δH (400 MHz, DMSO) 2.46 (3H, s), 4.64 (2H, s), 5.75 (2H, s), 6.50 (1H, d, J 3.5 Hz), 7.04 (1H, d, J 8.0 Hz), 7.31 (2H, s), 7.49 (1H, d, J 7.5 Hz), 7.80 (1H, t, J 7.5 Hz), 7.88 (1H, d, J 3.5 Hz). TLC (Hexane:EtOAc (1:1)) Rf=0.28**

Sources & evidence

ORD record
ord-d1139357c58f4b068d309b7e92a55f89
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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