Diisopropylethylamine → HCID 58169319, compound

HRID 1484950Notes

Reaction equation

HRID 1484950 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:8](Br)=[N:9][C:10]([Br:13])=[N:11][CH:12]=1)(=[O:3])[CH3:2].[CH:15]1([C:18]2[NH:22][N:21]=[C:20]([NH2:23])[CH:19]=2)[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>CC(O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:8]([NH:23][C:20]2[CH:19]=[C:18]([CH:15]3[CH2:17][CH2:16]3)[NH:22][N:21]=2)=[N:9][C:10]([Br:13])=[N:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 58169472HCID 58169472, compound

Product 1

HCID 58169319HCID 58169319, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(2,4-dibromopyrimidin-5-yl)ethyl acetate (650 mg, 2.0 mmol, 1.0 eq), 5-cyclopropyl-1H-pyrazol-3-amine (296 mg, 2.4 mmol, 1.2 eq) and DIPEA (387 mg, 3.0 mmol, 1.5 eq) in propan-2-ol (10 mL) was stirred at 60° C. for 16 h. The mixture was extracted with EtOAc. The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to give a residue, which was purified by silica gel column chromatography (PE/EtOAc=1:2) to give 2-(2-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)ethyl acetate (390 mg, 53%) as a white solid. LC-MS (m/z)=366 [M+H]+

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic phases were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customwas purified by silica gel column chromatography (PE/EtOAc=1:2)

Sources & evidence

ORD record
ord-5c62cb3bc18d4d65a1c91259e0d6b5bc
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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