3-(Dimethylamino)-2-propenal → 3-[4-(Trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-2-amine

HRID 1912890Notes

Reaction equation

HRID 1912890 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([NH2:16])=[N:12][NH:13][C:14]=2[NH2:15])=[CH:6][CH:5]=1.CN(C)[CH:21]=[CH:22][CH:23]=O>C(O)C.C(O)(=O)C>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([NH2:15])=[N:13][N:12]3[CH:23]=[CH:22][CH:21]=[N:16][C:11]=23)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 791253-(Dimethylamino)-2-propenalHCID 687542964-(4-(trifluoromethoxy)phenyl)-1H-pyrazole-3,5-diamine

Product 1

HCID 687492143-[4-(Trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-2-amineYield 107.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

In a microwave vessel containing the product from Example 1B (0.4 g, 1.549 mmol) and 3-(dimethylamino)acrylaldehyde (0.155 g, 1.549 mmol) in ethanol (5 mL) was added two drops of acetic acid. The mixture was irradiated with microwave at 140° C. for 15 minutes and concentrated. The resulting solid was purified by flash chromatography on silica gel, eluting with EtOAc/Hexanes (40-70% gradient), to yield the title compound (0.49 g, 59%). MS ESI+ m/z 295.5 [M+H]+.

Workup

  1. customThe mixture was irradiated with microwave at 140° C. for 15 minutes
  2. concentrationconcentrated
  3. customThe resulting solid was purified by flash chromatography on silica gel
  4. washeluting with EtOAc/Hexanes (40-70% gradient)

Sources & evidence

ORD record
ord-f0fecb6dd45c48a8a15c86580ab1ece0
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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