2-Chloro-5-nitropyrimidine → HCID 66631372, compound

HRID 544838Notes

Reaction equation

HRID 544838 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][CH2:3][CH2:2]2.Cl[C:11]1[N:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[N+:17]([C:14]1[CH:13]=[N:12][C:11]([N:4]2[CH:5]3[CH2:8][CH2:9][N:1]([CH2:7][CH2:6]3)[CH2:2][CH2:3]2)=[N:16][CH:15]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 825442-Chloro-5-nitropyrimidineHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 516892Sodium Bicarbonate

Product 1

HCID 66631372HCID 66631372, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,4-diazabicyclo[3.2.2]nonane (0.87 g, 6.90 mmol), 2-chloro-5-nitro-pyrimidine (1.56 g, 6.27 mmol) and dioxane (75 ml) was stirred at room-temperature for 15 h. Aqueous sodium bicarbonate (20 ml, 10%) was added followed by extraction with ethylacetate (3×20 ml). The organic phase was dried and evaporated and a yellow powder was isolated. Yield 0.86 g (55%). Mp 135-139° C.

Workup

  1. extractionfollowed by extraction with ethylacetate (3×20 ml)
  2. customThe organic phase was dried
  3. customevaporated
  4. customa yellow powder was isolated

Sources & evidence

ORD record
ord-db179f7c42db4ba0b5e0c3cd9209b495
Source dataset
uspto-grants-2011_05
Patent number
US07935695B2

Reaction notes

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