Diisopropylethylamine → HCID 21934672, compound

HRID 1241364Notes

Reaction equation

HRID 1241364 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:18][O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(O)CCC>[CH3:18][O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2380124-Amino-6-chloropyrimidineHCID 27346381-(2-Methoxyethyl)piperazine

Product 1

HCID 21934672HCID 21934672, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
125 °C

Procedure

6-Chloropyrimidin-4-amine 7-2 (0.3 g, 2.32 mmol) and diisopropylethylamine (0.30 g, 2.32 mmol) were suspended in n-butanol and then 1-(2-methoxyethyl)piperazine 5-2 (0.334 g, 2.32 mmol) was added. The reaction was stirred at 125° C. for 18 hours. The butanol was removed under reduced pressure, diluted with DCM and loaded onto a silica column eluted with DCM (100 mL), DCM:MeOH (99:4) and then DCM:MeOH:NH4OH (9:1:0.1). The product 5-3 was isolated after evaporation. 1H-NMR (DMSO): 7.95 ppm (s, 1H); 6.23 ppm (s, 2H); 5.59 ppm (s, 1H); 3.43 ppm (m, 4H); 3.33 ppm (m, 2H); 3.25 ppm (s, 3H); 2.59 ppm (m, 2H); 2.54 ppm (m, 4H).

Workup

  1. customThe butanol was removed under reduced pressure
  2. additiondiluted with DCM
  3. washeluted with DCM (100 mL), DCM:MeOH (99:4)

Sources & evidence

ORD record
ord-1e02db77e1c24b65ab44f24d9e983162
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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