Ethyl Acetate → HCID 118162129, compound

HRID 1749413Notes

Reaction equation

HRID 1749413 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:7][CH:6]([NH2:8])[C:5]1([CH3:10])[CH3:9])[CH3:2].Cl[C:12]1[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(O)(C)(C)C.ClCCCl>[CH2:1]([O:3][CH:4]1[CH2:7][CH:6]([NH:8][C:12]2[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=2)[C:5]1([CH3:10])[CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 536199383-ethoxy-2,2-dimethylcyclobutan-1-amine

Product 1

HCID 118162129HCID 118162129, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21868497Tert-butyl alcohol 1,2-dichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-ethoxy-2,2-dimethylcyclobutanamine (1.0 equiv.) and 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (1.1 equiv.) in tert-butanol/1,2-dichloroethane (0.5 M) was treated with potassium carbonate powder (3.0 equiv.). The resulting reaction mixture was then heated at 70° C. under nitrogen for 3 h. After cooling, ethyl acetate was added and the mixture was vigorously stirred. The solid was removed by vacuum-filtration. The filtrate was concentrated and further dried to give (100% yield) of waxy, yellow solid, which was used in the next step without further purification. MS (ESI) m/z 293.0 [M+1]+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling
  3. customThe solid was removed by vacuum-filtration
  4. concentrationThe filtrate was concentrated
  5. customfurther dried
  6. customto give (100% yield) of waxy, yellow solid, which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-faf4807f230e43769abb6eaa025388a4
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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