Diisopropylethylamine → HCID 90121138, compound

HRID 521720Notes

Reaction equation

HRID 521720 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:14]3([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH2:15][NH:16][CH2:17][CH:13]3[CH2:12][O:11]2)=[CH:5][CH:4]=1.Cl[C:25]1[N:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[F:31][C:28]1[CH:27]=[N:26][C:25]([N:16]2[CH2:17][CH:13]3[C:14]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)([N:10]([CH2:9][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[O:11][CH2:12]3)[CH2:15]2)=[N:30][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5834662-Chloro-5-fluoropyrimidineHCID 90111297HCID 90111297, compound

Product 1

HCID 90121138HCID 90121138, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 1-[(4-methoxyphenyl)methyl]-6a-(3-pyridyl)-3a,4,5,6-tetrahydro-3H-pyrrolo[3,4-c]isoxazole (1.33 g, 4.27 mmol) in 1,4-dioxane (30 mL) is added 2-chloro-5-fluoro-pyrimidine (2.55 g, 19.22 mmol) and diisopropylethylamine (3.72 mL, 21.36 mmol). The resulting solution is heated at 110° C. for 3 hours. The reaction is cooled and the solvent is evaporated under vacuum to give a residue. The residue is purified by silica gel chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (1.11 g, 54%). ES/MS (m/e): 408 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvent is evaporated under vacuum
  3. customto give a residue
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e58cec6c60945daabda5e2955ac0a40
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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