3-(Dimethylamino)-2-propenal → 3-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amine

HRID 1912908Notes

Reaction equation

HRID 1912908 reaction equation
[C:1]([C:5]1[C:6]([NH2:11])=[N:7][NH:8][C:9]=1[NH2:10])([CH3:4])([CH3:3])[CH3:2].CN(C)[CH:14]=[CH:15][CH:16]=O>C(O)C.C(O)(=O)C>[C:1]([C:5]1[C:6]([NH2:11])=[N:7][N:8]2[CH:16]=[CH:15][CH:14]=[N:10][C:9]=12)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 791253-(Dimethylamino)-2-propenalHCID 68753336HCID 68753336, compound

Product 1

HCID 687554713-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amineYield 72.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture from Example 105A (2.61 g, 16.9 mmol), 3-dimethylaminoacrylaldehyde (2.0 mL, 20.0 mmol) and acetic acid (25 μL, 0.44 mmol) in ethanol (18 mL) was heated by microwave to 150° C. for 30 minutes. The mixture was cooled to ambient temperature and concentrated. Purification by silica gel chromatography (EtOAc, Rf=0.39) afforded 2.34 g (43%) of the title compound. MS (DCI) m/z 191 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customPurification by silica gel chromatography (EtOAc, Rf=0.39)

Sources & evidence

ORD record
ord-15598afda19948d0904f9d8635cab8ee
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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