tert-Butanol → N2-(1',3-dimethyl-1'H-1,4'-bipyrazol-4-yl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 1503301Notes

Reaction equation

HRID 1503301 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[CH:11]=[C:10]([NH2:12])[C:9]([CH3:13])=[N:8]2)[CH:4]=[N:3]1.Cl[C:15]1[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[CH:17][N:16]=1.[CH3:27]C(O)(C)C>>[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:11]([CH3:27])=[C:10]([NH:12][C:15]3[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[CH:17][N:16]=3)[CH:9]=[N:8]2)[CH:4]=[N:3]1.[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[CH:11]=[C:10]([NH:12][C:15]3[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:24])[F:25])=[CH:17][N:16]=3)[C:9]([CH3:13])=[N:8]2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 210775872-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amineHCID 916189261',3-dimethyl-1'H-1,4'-bipyrazol-4-amine

Product 2

HCID 69281779N2-(1',5-dimethyl-1'H-1,4'-bipyrazol-4-yl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamineYield 17%HCID 69281780N2-(1',3-dimethyl-1'H-1,4'-bipyrazol-4-yl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamineYield 26%

Conditions

Temperature
100 °C

Procedure

A microwave vial equipped with a magnetic stirrer was charged with the mixture of 1%5-dimethyl-1′H-1,4′-bipyrazol-4-amine and 1′,3-dimethyl-1′H-1,4′-bipyrazol-4-amine (50 mg, 0.28 mmol), 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (60 mg, 0.28 mmol), and t-BuOH (3 mL). The mixture was heated at 100° C. under microwave irradiation for 1 h. After removal of the volatiles, the residue was purified by prep-HPLC to afford N2-(1′,5-dimethyl-1′H-1,4′-bipyrazol-4-yl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (17 mg, 17%) as a white solid and N2-(1′,3-dimethyl-1′H-1,4′-bipyrazol-4-yl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (26 mg, 26%) as a white solid.

Workup

  1. customA microwave vial equipped with a magnetic stirrer
  2. customAfter removal of the volatiles
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-85ae70a6b34c47e291e1ccf2ee161c42
Source dataset
uspto-grants-2015_12
Patent number
US09212173B2

Reaction notes

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