4-Pyrimidinamine, 6-chloro-5-nitro- → HCID 67132852, compound

HRID 1712893Notes

Reaction equation

HRID 1712893 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+]([O-])=O.Cl.Cl.[NH2:14][CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)=[O:18]>C1COCC1.C(O)C.O>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:17](=[O:18])[CH2:16][CH2:15][NH:14][C:2]2[CH:3]=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 1012294-Pyrimidinamine, 6-chloro-5-nitro-HCID 67133183HCID 67133183, compound

Product 1

HCID 67132852HCID 67132852, compoundYield 101.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6-Chloro-5-nitro-pyrimidin-4-ylamine (379 mg, 2.1 mmol) in THF (2 mL) was added to an ice cold solution of Example 9B (510 mg, 2.1 mmol) in THF (20 mL) and ethanol (20 mL). The mixture was stirred at 0 C for 20 min, at room temperature for 1 hr and heated at 75 C for 2 h. The mixture was allowed to cool to room temperature, diluted with water (50 mL), concentrated, and filtered. The filter cake was washed with water and dried to give 0.55 g (83% yield) of the title compound. MS(ESI(+)) m/e 303.0 (M+H)+.

Workup

  1. temperatureheated at 75 C for 2 h
  2. temperatureto cool to room temperature
  3. concentrationconcentrated
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-45169e0190ac49ab99861d5c950e9ce8
Source dataset
uspto-grants-2010_09
Patent number
US07795248B2

Reaction notes

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