1,2-Dibromoethane → HCID 86699682, compound

HRID 1487186Notes

Reaction equation

HRID 1487186 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][C:10]([O:12]CC)=O)=[C:4]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33]Br>>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]2[C:9]3([CH2:33][CH2:32]3)[C:10](=[O:12])[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 86699674HCID 86699674, compound

Product 1

HCID 86699682HCID 86699682, compoundYield 82.7%

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-(2,4-dichloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate (27.1 g, 73.2 mmol) and powder potassium carbonate (101.1 g, 732.4 mmol) in N,N-dimethyllformamide (800 mL) was added 1,2-dibromoethane (27.5 g, 146.4 mmol) dropwise under nitrogen atmosphere at 40° C. After the addition was over, the reaction mixture was heated to 80° C. for 1 h. Quenched with water, extracted with ethyl acetate, and the organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product as a snow-white solid (21.2 g, yield 82.7%). 1H NMR (400 MHz, CDCl3) δ ppm 7.53-7.38 (m, 2H), 6.86 (dd, J=8.4, 1.3 Hz, 2H), 4.94 (d, J=0.8 Hz, 2H), 3.79 (d, J=1.6 Hz, 3H), 2.14 (qd, J=4.3, 1.6 Hz, 2H), 1.79 (qd, J=4.3, 1.6 Hz, 2H).

Workup

  1. additionAfter the addition
  2. customQuenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-04194d46a21e40abbd68ab61edfd9590
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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