Diisopropylethylamine → HCID 86731669, compound

HRID 1504775Notes

Reaction equation

HRID 1504775 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[N:11]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:8][C:6]1[N:5]=[C:4]([NH2:9])[CH:3]=[C:2]([N:10]2[CH:14]=[CH:13][N:12]=[N:11]2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 190505094-Chloro-6-methylpyridin-2-amineHCID 178418936HCID 178418936, compound

Product 1

HCID 86731669HCID 86731669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To 4-chloro-6-methylpyridin-2-amine (100 mg, 0.701 mmol) and 1,2,3-triazole (0.133 mL, 2.30 mmol) in a pressure tube was added DIPEA (0.185 mL, 1.06 mmol). The reaction mixture was sealed and heated at 150° C. for 1.5 hours. The reaction mixture was cooled, diluted with DCM (20 mL), and washed with water (10 mL). The organics were separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was slurried in 5% methanol/ethyl acetate (5 mL) and sonicated. The mixture was filtered, and the collected solids were dried under reduced pressure to afford 6-methyl-4-(1H-1,2,3-triazol-1-yl)pyridin-2-amine. MS ESI calc'd. for C8H10N5 [M+H]+ 176. found 176. 1H NMR (500 MHz, DMSO-d6) δ 8.79 (s, 1H), 7.95 (s, 1H), 6.90 (s, 1H), 6.75 (s, 1H), 6.28 (s, 2H), 2.23 (s, 3H).

Workup

  1. customThe reaction mixture was sealed
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water (10 mL)
  4. customThe organics were separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customsonicated
  9. filtrationThe mixture was filtered
  10. customthe collected solids were dried under reduced pressure

Sources & evidence

ORD record
ord-53c8f0429902452fbc9303e4becae7bb
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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