3-Chloro-2,5-diethylpyrazine → 3-Chloro-5-cyclopropyl-2-methylpyrazine

HRID 1612327Notes

Reaction equation

HRID 1612327 reaction equation
[Cl:1][C:2]1[C:3]([CH2:10][CH3:11])=[N:4][CH:5]=[C:6]([CH2:8]C)[N:7]=1.[CH:12]1([CH:15]2[NH:20][C:19](=O)[CH:18]([CH3:22])[NH:17][C:16]2=O)[CH2:14][CH2:13]1>>[Cl:1][C:2]1[C:3]([CH:10]2[CH2:11][CH2:12]2)=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1.[Cl:1][C:19]1[C:18]([CH3:22])=[N:17][CH:16]=[C:15]([CH:12]2[CH2:14][CH2:13]2)[N:20]=1

Participants

4

Reactant 2

HCID 2373953-Chloro-2,5-diethylpyrazineHCID 221473683-Cyclopropyl-6-methylpiperazine-2,5-dione

Product 2

HCID 221473143-Chloro-5-cyclopropyl-2-methylpyrazineHCID 221475313-Chloro-2-cyclopropyl-5-methylpyrazine

Procedure

Following the procedure for the preparation of 3-chloro-2,5-diethylpyrazine but substituting 3-cyclopropyl-6-methylpiperazine-2,5-dione and making non-critical variations provided 3-chloro-2-cyclopropyl-5-methylpyrazine (A) and 3-chloro-5-cyclopropyl-2-methylpyrazine (B) as oils. Analytical data for 3-chloro-2-cyclopropyl-5-methylpyrazine (A): 1H NMR (CDCl3) δ 1.44, 2.35, 2.90, 3.07, 8.10; MS (ESI+) for C8H9N2Cl m/z 169 (M+H)+; Analytical data for 3-chloro-5-cyclopropyl-2-methylpyrazine (B): 1H NMR (CDCl3) δ 1.04, 2.00, 2.57, 8.10; MS (ESI+) for C8H9N2Cl m/z 169 (M+H)+.

Sources & evidence

ORD record
ord-7885f9ce32b24f388fff85660174ba8e
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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