Water → HCID 58654334, compound

HRID 1170537Notes

Reaction equation

HRID 1170537 reaction equation
[CH3:1][NH2:2].[N:3]1([C:8]2[N:13]=[C:12]([CH:14]3[CH:18]([C:19]([O:21]CC)=O)[CH2:17][CH2:16][N:15]3[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:11]=[C:10]([CH3:31])[N:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.O>C1COCC1>[N:3]1([C:8]2[N:13]=[C:12]([CH:14]3[CH:18]([C:19](=[O:21])[NH:2][CH3:1])[CH2:17][CH2:16][N:15]3[C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH:11]=[C:10]([CH3:31])[N:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 58654352HCID 58654352, compound

Product 1

HCID 58654334HCID 58654334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Methylamine (35 mL of a 25 wt % solution in THF) was added all at once to a solution of 1-tert-butyl 3-ethyl 2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)pyrrolidine-1,3-dicarboxylate (650 mg, 1.6 mmol) in THF (30 mL). The reaction mixture was heated to 60° C. for a period 12 h then cooled to rt. Water (50 mL) was added and the resulting solution was extracted with EtOAc (3×10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford tert-butyl 2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-(methylcarbamoyl)pyrrolidine-1-carboxylate (620 mg) as yellow oil.

Workup

  1. temperaturethen cooled to rt
  2. extractionthe resulting solution was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7c5a6b9ba5e1445b9c02fb65f36e5bc1
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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