2-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine → HCID 178428253, compound

HRID 475290Notes

Reaction equation

HRID 475290 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.Cl.O1CCCCC1[N:22]1[C:26]2[CH:27]=[CH:28][C:29]([C@@H:31]([NH2:33])[CH3:32])=[CH:30][C:25]=2[N:24]=[CH:23]1>CCCCO>[NH:22]1[C:26]2[CH:27]=[CH:28][C:29]([C@@H:31]([NH:33][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=4)[CH:5]=[CH:4][N:3]=3)[CH3:32])=[CH:30][C:25]=2[N:24]=[CH:23]1

Participants

4

Reactant 2

HCID 231324822-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 86694728HCID 86694728, compound

Product 1

HCID 178428253HCID 178428253, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 2-chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (105 mg, 0.5 mmol) in n-BuOH (2 mL) in a microwave vial was added 126 (184 mg, 0.75 mmol). To the solution was added dropwise TEA (0.21 mL, 1.5 mmol) and the vial sealed and irradiated in a in the microwave synthesizer at 110° C. for 6 h. The solvent was evaporated under reduced pressure and the crude residue was taken up in DCM (5 mL) and MeOH (5 mL) and the solvent was again concentrated in vacuo. The residue was diluted in DMF (1 mL) and filtered. The crude mixture was purified by reverse phase HPLC to afford 9 mg (5%) of I-121.

Workup

  1. customthe vial sealed
  2. customirradiated in a in the microwave synthesizer at 110° C. for 6 h
  3. customThe solvent was evaporated under reduced pressure
  4. concentrationMeOH (5 mL) and the solvent was again concentrated in vacuo
  5. additionThe residue was diluted in DMF (1 mL)
  6. filtrationfiltered
  7. customThe crude mixture was purified by reverse phase HPLC
  8. customto afford 9 mg (5%) of I-121

Sources & evidence

ORD record
ord-9533f86c249340dfb14e0773ba11f379
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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