2-Bromoethanol → HCID 57961676, compound

HRID 541951Notes

Reaction equation

HRID 541951 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[CH:6]=[C:7]([SH:11])[CH:8]=[CH:9][CH:10]=1.Br[CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[N:28]=[C:27](Cl)[C:26]([Cl:30])=[CH:25][N:24]=1>CN(C)C=O.O.[Cl-].[Na+].O>[Cl:22][C:23]1[N:28]=[C:27]([NH:4][C:5]2[CH:6]=[C:7]([S:11][CH2:13][CH2:14][OH:15])[CH:8]=[CH:9][CH:10]=2)[C:26]([Cl:30])=[CH:25][N:24]=1

Participants

8

Reactant 5

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 315773-AminothiophenolHCID 2372592,4,5-TrichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 57961676HCID 57961676, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 23713072Sodium chloride dihydrateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of sodium methoxide (2.4 g, 44 mmol) in N,N-dimethylformamide (80 mL) was treated with 3-aminobenzenethiol (4.6 g, 37 mmol) and stirred at 20° C. for 15 min. The reaction mixture was cooled to 0° C., treated with a solution of 2-bromoethanol (3.4 mL, 48 mmol) in N,N-dimethylformamide (10 mL), and stirred at 0° C. for 15 min and at 20° C. for 1 h. The reaction mixture was treated with potassium carbonate (10 g, 74 mmol) followed by 2,4,5-trichloropyrimidine (5.5 mL, 48 mmol), heated at 60° C. for 1 h, and stirred at 20° C. for 16 h. The reaction mixture was diluted with 4:1 water/brine (1 L) and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with water (3×300 mL) and brine, dried over anhydrous sodium sulfate, filtered, and evaporated to a crude brown oil. This material was purified by flash column chromatography to give the desired product (7.8 g, 68%) as a solid after lyophilization. LCMS for C12H12Cl2N3OS (M+H)+: m/z=315.9, 317.9.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringstirred at 0° C. for 15 min and at 20° C. for 1 h
  3. temperatureheated at 60° C. for 1 h
  4. stirringstirred at 20° C. for 16 h
  5. extractionextracted with ethyl acetate (2×250 mL)
  6. washThe combined organic layers were washed with water (3×300 mL) and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated to a crude brown oil
  10. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-ecfe5a11bd25442ebd1f0cb413301268
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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