Triethylamine → HCID 89560715, compound

HRID 530126Notes

Reaction equation

HRID 530126 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:5]([NH2:14])=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[C:23](=[O:29])[C:24](OCC)=[O:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:14][C:24](=[O:25])[C:23](=[O:29])[N:8]([CH2:9][CH2:10][CH:11]([CH3:12])[CH3:13])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 89561473HCID 89561473, compound

Product 1

HCID 89560715HCID 89560715, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-chloro-N4-(3-methylbutyl)pyrimidine-4,5-diamine (2.8 g, 13.08 mmol) in toluene (40 mL) was added triethylamine (4.23 g, 41.88 mmol) and ethyl chlorooxoacetate (1.95 g, 14.33). The mixture was then heated to reflux for 16 h. It was then cooled to rt, the bulk of solvent was removed under reduced pressure to give a crude residue, which was purified by silica gel column chromatography (eluent: 70% ethyl acetate in hexane) afforded the desired product (2.1 g). 1H NMR (CDCl3, 300 MHz) δ 1.01 (d, J=6.6 Hz, 6H), 1.60-1.82 (m, 3H), 4.20-4.35 (m, 2H), 8.35 (s, 1H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 16 h
  3. customthe bulk of solvent was removed under reduced pressure
  4. customto give a crude residue, which
  5. customwas purified by silica gel column chromatography (eluent: 70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7afd1d32dc774f0f8dd621e8fe916b03
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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