Acetic Acid → HCID 178453907, compound

HRID 1050944Notes

Reaction equation

HRID 1050944 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O=[CH:22][CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:26][CH2:25]1.CC(O)=O.[Na]>ClCCCl.O>[C:1]([C:5]1[N:6]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:22][CH2:23][C@H:24]3[CH2:25][CH2:26][C@H:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:28][CH2:29]3)[CH2:17][CH2:16]2)[CH:8]=[C:9]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 666733902-tert-Butyl-4-cyclobutyl-6-(piperazin-1-yl)pyrimidineHCID 178453924HCID 178453924, compound

Product 1

HCID 178453907HCID 178453907, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A mixture of 2-tert-butyl-4-cyclobutyl-6-(piperazin-1-yl)pyrimidine (7.16 g, 26.1 mmol) and tert-butyl trans-4-(2-oxoethyl)cyclohexylcarbamate (6 g, 24.86 mmol) in DCE (100 ml) was stirred at room temperature for 10 min. AcOH and sodium triacetoxyhydroborate (7.90 g, 37.3 mmol) were added. After 4 h, water was added. The aqueous layer was extracted with methylene chloride (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound as a yellow oil of (11.2 g, 21.29 mmol, 86% yield) which was used next step without purification.

Workup

  1. waitAfter 4 h
  2. extractionThe aqueous layer was extracted with methylene chloride (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25b6ffdfaac543a9813b78e308bd8429
Source dataset
uspto-grants-2016_07
Patent number
US09388141B2

Reaction notes

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