1-Butanol → methyl 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylate

HRID 2409100Notes

Reaction equation

HRID 2409100 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([Cl:10])=[CH:4][N:3]=1.[NH2:11][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:13]=1.C(O)CCC.Cl>O1CCOCC1>[Cl:10][C:5]1[C:6]([NH:8][CH3:9])=[N:7][C:2]([NH:11][C:12]2[N:16]([CH3:17])[N:15]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:13]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 13324840methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylateHCID 189812472,5-dichloro-N-methylpyrimidin-4-amine

Product 1

HCID 69081130methyl 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylateYield 64.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a 30 mL microwave vial was added 0.98 g of 2,5-dichloro-N-methylpyrimidin-4-amine, 0.78 g of methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate, 10 mL of 1-butanol and 0.13 mL of 4M hydrogen chloride in dioxane. The vial was capped and the reaction was heated in a microwave for 30 minutes at 130° C. As the reaction cooled, a precipitate fell out. Filter the precipitate and rinse with a small amount of n-butanol. Drying the cake yielded 0.964 g of methyl 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylate which was used without further purification.

Workup

  1. customThe vial was capped
  2. temperatureAs the reaction cooled
  3. filtrationFilter the precipitate
  4. washrinse with a small amount of n-butanol
  5. customDrying the cake

Sources & evidence

ORD record
ord-3bf2c040ccb84b0d959337fc1d1d89e3
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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