Isopropylamine → 2-Chloro-6-isopropylaminopyrazine

HRID 634255Notes

Reaction equation

HRID 634255 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH:9]([NH2:12])([CH3:11])[CH3:10].CCN(CC)CC>C1COCC1>[Cl:8][C:4]1[N:3]=[C:2]([NH:12][CH:9]([CH3:11])[CH3:10])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 263700242-Chloro-6-isopropylaminopyrazineYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2,6-dichloropyrazine (5 g, 33.78 mmolm, Aldrich) and isopropyl amine (2.4 g, 50.67 mmol, Aldrich) in dry THF (5 mL) was added Et3N (2.5 mL) and the reaction was stirred at 60° C. for 12 h. The reaction was cooled to RT, treated with ice cold water (˜25 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was triturated with n-pentane to give 6-chloro-N-isopropylpyrazin-2-amine (3 g, 52.5%) as a white solid. MS (ESI, pos. ion) m/z: 172.0 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.64 (s, 1H), 7.46 (d, J=7.2 Hz, 1H), 3.93-3.88 (m, 1H), 1.15 (d, J=5.6 Hz, 6H).

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was triturated with n-pentane

Sources & evidence

ORD record
ord-b733919a750b4dcb92ec1eba583d1b3e
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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