Triethylamine → 2-Methyl-4-(5-phenylethynyl-pyrazin-2-ylamino)-butan-2-ol

HRID 1894265Notes

Reaction equation

HRID 1894265 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]([CH3:23])([OH:22])[CH3:21].C(N(CC)CC)C>N1C=CC=CC=1>[CH3:21][C:20]([OH:22])([CH2:19][CH2:18][NH:17][C:2]1[CH:7]=[N:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1)[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 426145604-Amino-2-methylbutan-2-ol hydrochlorideHCID 575167832-Bromo-5-phenylethynyl-pyrazine

Product 1

HCID 575167842-Methyl-4-(5-phenylethynyl-pyrazin-2-ylamino)-butan-2-olYield 509.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-bromo-5-(phenylethynyl)pyrazine (Example 168, step 1) (158 mg, 0.061 mmol) and 4-amino-2-methylbutan-2-ol hydrochloride (255 mg, 1.83 mmol, 30 equiv.) and triethylamine (185 mg, 255 ul, 1.83 mmol, 30 equiv.) in 3 ml pyridine was stirred overnight at 85° C. The reaction mixture was concentrated in vacuo. After workup with dichloromethane/water/brine, and drying over magnesium sulfate, the organic phases were concentrated in vacuo. The crude product was chromatographed over a prepacked 20 g silica column eluting with a 25% to 100% ethyl acetate in heptane gradient which yielded the title compound (87.5 mg, 51% yield) as an off-white solid, MS: m/e=282.2 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dry with materialAfter workup with dichloromethane/water/brine, and drying over magnesium sulfate
  3. concentrationthe organic phases were concentrated in vacuo
  4. customThe crude product was chromatographed over a prepacked 20 g silica column
  5. washeluting with a 25% to 100% ethyl acetate in heptane gradient which

Sources & evidence

ORD record
ord-98ecc2493e5a4dcb892a80331c78dba3
Source dataset
uspto-grants-2013_08
Patent number
US08513273B2

Reaction notes

Loading…