Urea → HCID 347395, compound

HRID 709436Notes

Reaction equation

HRID 709436 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[CH3:5][C:6]1[N:11]=[C:10](N)[CH:9]=[CH:8][CH:7]=1>>[CH3:5][C:6]1[N:11]=[C:10]([NH:1][C:2]([NH2:4])=[O:3])[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 157652-Amino-6-methylpyridine

Product 1

HCID 347395HCID 347395, compoundYield 32.2%

Conditions

Temperature
145 °C

Procedure

To a 25-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was added urea (1.48 g, 24.64 mmol, 1.00 equiv) and 6-methylpyridin-2-amine (3 g, 27.74 mmol, 1.00 equiv). The resulting mixture was stirred for 2 h at 145° C. After cooling, the crude product (4 g) was purified using CombiFlash: Column, C18 silica gel; utilizing a mobile phase of CH3CN: H2O=0:100 to CH3CN: H2O=50:50 over 40 min. This resulted in the isolation of 1.2 g (32%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ ppm 9.07 (s, 1H), 7.56-7.52 (m, 1H), 7.18-7.14 (m, 1H), 6.80-6.75 (m, 1H), 2.36 (s, 3H).

Workup

  1. customTo a 25-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of argon
  3. temperatureAfter cooling
  4. customthe crude product (4 g) was purified
  5. waitH2O=0:100 to CH3CN: H2O=50:50 over 40 min

Sources & evidence

ORD record
ord-6e4bec3eb2b74978bd102f662d807615
Source dataset
uspto-grants-2015_11
Patent number
US09181200B2

Reaction notes

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