Pyrimidin-5-amine → HCID 25069284, compound

HRID 253697

Reaction equation

HRID 253697 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=3)=[N:7][O:8][C:4]=2[C:3]=1[C:20](O)=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:47]1[CH:52]=[C:51]([NH2:53])[CH:50]=[N:49][CH:48]=1>CN(C=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH2:16][CH3:17])=[CH:14][CH:15]=3)=[N:7][O:8][C:4]=2[C:3]=1[C:20]([NH:53][C:51]1[CH:52]=[N:47][CH:48]=[N:49][CH:50]=1)=[O:21]

Participants

5

Reactant 3

HCID 344373Pyrimidin-5-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59805814HCID 59805814, compound

Product 1

HCID 25069284HCID 25069284, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

6-Chloro-3-(4-ethylphenylamino)benzo[d]isoxazole-7-carboxylic acid (0.195 g, 0.615 mmol) was dissolved in DMF, followed by TEA (0.223 ml, 1.61 mmol) and HATU (0.285 g, 0.749 mmol). The mixture was allowed to stir for 5 min before adding pyrimidin-5-amine (0.0509 g, 0.535 mmol) and the mixture was heated to 50° C. overnight. The mixture was then cooled to RT, partitioned between EtOAc/brine, the layers were separated, and the aqueous was extracted with EtOAc (3×). The combined organics were washed with H2O and brine, filtered and concentrated. The crude material was purified by silica gel chromatography using 20:1 DCM/MeOH to give 6-Chloro-3-(4-ethylphenylamino)-N-(pyrimidin-5-yl)benzo[d]isoxazole-7-carboxamide as a light brown solid. MS calculated 393.8, found M+H+=394.1.

Workup

  1. temperatureThe mixture was then cooled to RT
  2. custompartitioned between EtOAc/brine
  3. customthe layers were separated
  4. extractionthe aqueous was extracted with EtOAc (3×)
  5. washThe combined organics were washed with H2O and brine
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ce198f69a904c0eabcad9423edb3693
Source dataset
uspto-grants-2011_01
Patent number
US07872128B2

Linked notes

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