2,6-dichloro-N-cyclobutyl-5-nitropyrimidin-4-amine → HCID 118073531, compound

HRID 928186Notes

Reaction equation

HRID 928186 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:12][CH2:11][CH2:10]2)[C:5]([N+:13]([O-])=O)=[C:4]([Cl:16])[N:3]=1>CC(O)=O.[Fe]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][CH2:12]2)[C:5]([NH2:13])=[C:4]([Cl:16])[N:3]=1

Participants

4

Reactant 1

HCID 1180736132,6-dichloro-N-cyclobutyl-5-nitropyrimidin-4-amine

Product 1

HCID 118073531HCID 118073531, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Fe powder (631 mg, 11.3 mmol) was added to a solution of 2,6-dichloro-N-cyclobutyl-5-nitropyrimidin-4-amine (crude, 5.65 mmol) in HOAc (5 mL) and the mixture was stirred at rt for 30 min. The mixture was filtered through Celite® and the volatiles were removed under reduced pressure. The resulting residue was diluted with EtOAc (80 mL) and washed with water (80 mL), sat. NaHCO3 (80 mL) and brine (80 mL). The organic layer was dried over Na2SO4 and concentrated to give the title compound as a brown oil which was used without purification. m/z (APCI+) for C8H10Cl2N4 233.15/235.10 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customthe volatiles were removed under reduced pressure
  3. additionThe resulting residue was diluted with EtOAc (80 mL)
  4. washwashed with water (80 mL), sat. NaHCO3 (80 mL) and brine (80 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd65cda710cd43e4a9084f9d42d5d79c
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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