Allyl Alcohol → HCID 21075393, compound

HRID 1373746Notes

Reaction equation

HRID 1373746 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[H-].[Na+].[NH2:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10](Cl)[N:9]=1>O1CCOCC1>[CH2:1]([O:4][C:10]1[N:9]=[C:8]([NH2:7])[CH:13]=[N:12][CH:11]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 21075393HCID 21075393, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of allyl alcohol (0.21 mL, 3.08 mmol) in dioxane (4 mL) was treated with NaH (60%, 3.08 mmol), stirred for 30 minutes, treated with 2-amino-6-chloropyrazine (200 mg, 1.54 mmol), heated to 140° C. in a Smith Synthesizer for 2200 seconds, and filtered. The filtrate was concentrated and purified by flash column chromatography eluting with hexanes/ethyl acetate (2:1) to provide the desired product (133 mg, 57%). MS (DCI/NH3) m/z 152.0 (M+H)+; 1H NMR (500 MHz, CD2Cl2) δ 4.75 (m, 2H), 5.24 (m, 1H), 5.37 (m, 1H), 6.05 (m, 1H), 7.50 (s, 1H), 7.53 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash column chromatography
  4. washeluting with hexanes/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-a924115265384afabb2aa21dd769372c
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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