Diisopropylethylamine → HCID 90112022, compound

HRID 521718Notes

Reaction equation

HRID 521718 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]12[CH2:14][NH:13][CH2:12][CH:11]1[CH2:10][O:9][NH:8]2.Cl[C:16]1[N:21]=[C:20]([O:22][CH3:23])[C:19]([F:24])=[C:18]([CH3:25])[N:17]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[F:24][C:19]1[C:20]([O:22][CH3:23])=[N:21][C:16]([N:13]2[CH2:12][CH:11]3[C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)([NH:8][O:9][CH2:10]3)[CH2:14]2)=[N:17][C:18]=1[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 582523322-Chloro-5-fluoro-4-methoxy-6-methylpyrimidineHCID 90112018HCID 90112018, compound

Product 1

HCID 90112022HCID 90112022, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 6a-pyrazin-2-yl-1,3,3a,4,5,6-hexahydropyrrolo[3,4-c]isoxazole (1.4 g, 7.28 mmol) in 1,4-dioxane (30 mL) is added 2-chloro-5-fluoro-4-methoxy-6-methyl-pyrimidine (5.14 g, 29.13 mmol) and diisopropylethylamine (5.7 mL, 32.77 mmol). The resulting solution is heated at 110° C. for 4 hours. The reaction is cooled and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (0.93 g, 38%). ES/MS (m/e): 333 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c84fc1ea2cc042e5b6a065b98130b5db
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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