(Prop-2-yn-1-yl)cyclohexane → 2-(3-cyclohexyl-prop-1-ynyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin

HRID 1808698Notes

Reaction equation

HRID 1808698 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.[CH:19]1([CH2:25][C:26]#[CH:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([CH2:25][C:26]#[C:27][C:2]2[N:3]=[C:4]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]3=[N:6][CH:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 87265(Prop-2-yn-1-yl)cyclohexaneHCID 575165972-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 581150342-(3-cyclohexyl-prop-1-ynyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazinYield 87.6%

Procedure

2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (402 mg, 1.22 mmol) and 3-cyclohexyl-1-propyne (745 mg, 6.1 mmol) were reacted under the same conditions as described in example 4 above. The crude product was adsorbed onto silica (1.5 g) and purified by silica gel chromatography, eluting with 5% to 20% ethyl acetate in hexanes to afford 395 mg of 2-(3-cyclohexyl-prop-1-ynyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin as a light brown semi-mobile oil. MS (M+H)+=370.

Workup

  1. custompurified by silica gel chromatography
  2. washeluting with 5% to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-57b8521f3f5f424d8124753f909070c6
Source dataset
uspto-grants-2013_01
Patent number
US08361962B2

Reaction notes

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