Hydrochloric Acid → HCID 86704212, compound

HRID 624031Notes

Reaction equation

HRID 624031 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([NH:11][C:12](=O)[CH2:13][N:14]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[N:15]2)[N:4]=1.Cl>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([NH:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[N:15]2)[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86704211HCID 86704211, compound

Product 1

HCID 86704212HCID 86704212, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To N-(4,5-dimethoxypyrimidin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide (318 mg, 1.03 mmol) in THF (2.0 mL), BH3 THF-complex solution (1 M in THF, 4.13 mL, 4.13 mmol) was added. After stirring at rt for 1.5 h, the reaction mixture was quenched with 1 N aq. HCl-solution (4 mL, 4 mmol) followed by concentrated HCl-solution (32%, 0.5 mL). After stirring for 10 min at rt, the reaction mixture was diluted with EtOAc, washed with sat. Na2CO3-solution. The aq. layer was reextracted with EtOAc and the comb. org. layers were evaporated, dissolved in DCM and washed with brine. The org. layer was dried (MgSO4), filtered and the solvent was removed by reduced pressure. Purification was performed by FC (EtOAc/hex 1:1 to 100% EtOAc) to yield 4,5-dimethoxy-N-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)pyrimidin-2-amine as a yellow solid. LC-MS conditions B: tR=0.43 min, [M+H]+=295.14.

Workup

  1. stirringAfter stirring for 10 min at rt
  2. washwashed with sat. Na2CO3-solution
  3. customlayers were evaporated
  4. dissolutiondissolved in DCM
  5. washwashed with brine
  6. dry with materiallayer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed by reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-b778e071581e4f2bab12c931d07295f9
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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