5-Amino-2,4-dichloropyrimidine → 2-Chloro-4-methoxypyrimidin-5-amine

HRID 2205954Notes

Reaction equation

HRID 2205954 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[N:10]=[C:9](Cl)[C:8]([NH2:12])=[CH:7][N:6]=1>CO.CCOC(C)=O>[Cl:4][C:5]1[N:10]=[C:9]([O:2][CH3:1])[C:8]([NH2:12])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 2577975-Amino-2,4-dichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 211863562-Chloro-4-methoxypyrimidin-5-amineYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium methoxide (0.5M in methanol, 3.7 mL, 1.829 mmol) was added to a solution of 2,4-dichloropyrimidin-5-amine (0.2 g, 1.220 mmol) in MeOH (2.5 mL). The reaction was stirred at room temperature for 1.5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177 mg, 91%). 1H NMR (500 MHz, CDCl3): δ 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 1.6 min, 160 [M+H]+

Workup

  1. customquenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29504f3ed7f04197ae1be911f62890be
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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