Triethylamine → HCID 86655328, compound

HRID 2096709Notes

Reaction equation

HRID 2096709 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]=[O:11])=[C:4]([Cl:12])[N:3]=1.[NH2:13][CH2:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:25][CH2:24][CH2:23][C:22]2=[O:26])[CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>CC(O)C>[NH2:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]([NH:9][CH:10]=[O:11])=[C:6]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])[N:20]=2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamideHCID 66718363HCID 66718363, compound

Product 1

HCID 86655328HCID 86655328, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (3.61 g, 17.43 mmol) and 1-(6-aminomethylpyridin-2-yl)pyrrolidin-2-one (containing triphenylphosphine oxide) (10.00 g, ca. 50 mmol) and triethylamine (4.86 mL, 34.86 mmol) in propan-2-ol (100 mL) was heated at reflux for 18 h, cooled and the resulting precipitate filtered to give the title compound (3.41 g) as an off-white solid; NMR δH (400 MHz, d6-DMSO) 9.21 (1H, s), 8.20 (1H, d, J 1 Hz), 8.12 (1H, d, J 8.5 Hz), 7.73 (1H, t, J 7.5 Hz), 7.38 (1H, t, J 6 Hz), 7.02 (1H, d, J 7.5 Hz), 6.45 (2H, br s), 4.53 (2H, d, J 6.0 Hz), 4.00-3.95 (2H, m), 2.57 (2H, t, J 8.0 Hz) and 2.08-2.00 (2H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. filtrationthe resulting precipitate filtered

Sources & evidence

ORD record
ord-403f06795dd84e17a8cc0dfd057c3088
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

Loading…