Diisopropylethylamine → HCID 86624841, compound

HRID 415431Notes

Reaction equation

HRID 415431 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:17][C:18]1[NH:22][N:21]=[C:20]([NH2:23])[CH:19]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:5]=[C:4]([NH:23][C:20]2[CH:19]=[C:18]([CH3:17])[NH:22][N:21]=2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 86624847HCID 86624847, compound

Product 1

HCID 86624841HCID 86624841, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2,6-dichloropyrimidin-4-yl)-N,N′,N′-trimethylsulfamide (Method 27, 1.72 g, 6.05 mmol) in n-BuOH (6 ml) was added 5-methyl-1H-pyrazol-3-amine (0.605 g, 6.05 mmol) and DIPEA (1.6 mL, 9.09 mmol). The mixture was heated at 70° C. overnight. The reaction mixture was filtered; the solid was washed by MeOH three times to give pure white solid. (0.205 g, 9.7% yield). LC-MS, 346 (M+1). NMR (DMSO-d6, 400 MHz, 80° C.) δ 11.89 (s, 1H), 9.82 (s, 1H), 7.22 (s, 1H), 5.97 (s, 1H), 3.32 (s, 3H), 2.87 (s, 6H), 2.21 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed by MeOH three times
  3. customto give pure white solid

Sources & evidence

ORD record
ord-776ad0de077142539f4a0aa727248f15
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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