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Water → Ethyl 3-cyclopropyl-3-(6-(((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)amino)pyrimidin-4-yl)propanoate

HRID 709617
Notes
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Reaction equation

HRID 709617 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][NH2:22])=[N:14][C:15]=1[O:16][CH2:17][CH:18]([CH3:20])[CH3:19].Cl[C:24]1[N:29]=[CH:28][N:27]=[C:26]([CH:30]([CH:37]2[CH2:39][CH2:38]2)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=1.C(N(CC)C(C)C)(C)C.O>C(#N)C>[CH:37]1([CH:30]([C:26]2[CH:25]=[C:24]([NH:22][CH2:21][C:13]3[CH:12]=[CH:11][C:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[F:1])=[C:15]([O:16][CH2:17][CH:18]([CH3:19])[CH3:20])[N:14]=3)[N:29]=[CH:28][N:27]=2)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:39][CH2:38]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1177599721-(5-(2-Fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanamineHCID 117760030Ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate

Product 1

HCID 117760162Ethyl 3-cyclopropyl-3-(6-(((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)amino)pyrimidin-4-yl)propanoate
Yield 54.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanamine (56 mg) and ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate (137 mg) in acetonitrile (3.0 mL) was added N,N-diisopropylethylamine (96 μL), and the mixture was stirred at 70° C. for 15 hr. Water was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified to by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (52 mg) as a colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified to by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fc7c359e13924c359ac94fc22f2c3551
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181186B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes