Ethanolamine → HCID 69671185, compound

HRID 626785

Reaction equation

HRID 626785 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[CH2:10]([CH2:12][NH2:13])[OH:11].CO>C(OCC)(=O)C>[NH2:9][C:4]1[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:13][CH2:12][CH2:10][OH:11])[CH:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 887MethanolHCID 2867546-Chloro-2-methylpyrimidin-4-amine

Product 1

HCID 69671185HCID 69671185, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 6-chloro-2-methylpyrimidin-4-ylamine (717 mg, 5.0 mmol) and ethanolamine (0.602 mL, 10.0 mmol) were heated at 250° C. in a microwave for 30 seconds. After cooling, the residue was dissolved in ethyl acetate, containing a small amount of methanol and was washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a white solid (334 mg, 40% yield). 1H NMR (400 MHz, DMSO-d6): δ 6.45 (br s, 1H), 5.98 (br s, 2H), 5.25 (s, 1H), 3.47 (t, J=6.0 Hz, 2H), 3.23-3.14 (m, 2H), 2.12 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. washwas washed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f4aad3310c7482bb8152eb6608ccce9
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Linked notes

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