Potassium Carbonate → HCID 86704210, compound

HRID 624027Notes

Reaction equation

HRID 624027 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][NH2:11])[CH:8]=1)([O-:3])=[O:2].CN1C(=O)CCC1.Cl[C:20]1[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:29][O:28][C:22]1[CH:23]=[C:24]([O:26][CH3:27])[N:25]=[C:20]([NH:11][CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]2)[N:21]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 51523232-Chloro-4,6-dimethoxypyrimidineHCID 70171364-Nitro-1H-pyrazole-1-ethanamine

Product 1

HCID 86704210HCID 86704210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A microwave tube was charged with 2-(4-nitro-1H-pyrazol-1-yl)ethanamine (1.92 g, 5.52 mmol), NMP. (15 mL), 2-chloro-4,6-dimethoxypyrimidine (1.16 g, 6.62 mmol) and K2CO3 (4.19 g, 30.34 mmol). The resulting mixture was heated to 150° C. for 20 min in the microwave (no cooling). The reaction mixture was diluted with DCM and washed with water. The org. layer was separated and the aq. layer was extracted with DCM (2×) The combined organic layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification was performed by FC (EtOAc/hept 6:4) to obtain 4,6-dimethoxy-N-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)pyrimidin-2-amine. LC-MS conditions A: tR=0.33 min, [M+H]+=no ionization.

Workup

  1. washwashed with water
  2. customlayer was separated
  3. extractionthe aq. layer was extracted with DCM (2×) The combined organic layers
  4. washwere washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customPurification

Sources & evidence

ORD record
ord-d0260648fa744537adfee05ec6dfa3ed
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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