Diisopropylethylamine → HCID 87339124, compound

HRID 75026Notes

Reaction equation

HRID 75026 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]([C:14]1([CH3:22])[CH2:19][CH2:18][CH2:17][CH:16]([NH2:20])[CH:15]1[OH:21])=[O:13].CCN(C(C)C)C(C)C>C1COCC1.CO>[CH3:10][O:11][C:12]([C:14]1([CH3:22])[CH2:19][CH2:18][CH2:17][CH:16]([NH:20][C:6]2[C:5]([F:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:15]1[OH:21])=[O:13]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 67284907Methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate

Product 1

HCID 87339124HCID 87339124, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-5-fluoro-pyrimidine (0.43 g, 2.58 mmol) and racemic methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate acetic acid salt, 66d, (0.58 g, 2.35 mmol) in THF (10 mL) and MeOH (8 mL) at room temperature was added iPr2NEt (1.23 mL, 7.04 mmol). After stirring the reaction overnight at room temperature, the solvent was evaporated under reduced pressure and the crude residue was purified by silica gel chromatography (Hexanes/EtOAc 100/0 to 0/100, Rf=0.7 in Hexanes/EtOAc 2/1) to provide 650 mg of racemic methyl-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]-2-hydroxy-1-methyl-cyclohexanecarboxylate, 66e, as a white solid. LCMS: 318.16 (M+1).

Workup

  1. customthe reaction overnight at room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customthe crude residue was purified by silica gel chromatography (Hexanes/EtOAc 100/0 to 0/100, Rf=0.7 in Hexanes/EtOAc 2/1)

Sources & evidence

ORD record
ord-c7216123d7b3477b8be81184234e8b96
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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