Acetone → HCID 86698312, compound

HRID 931696Notes

Reaction equation

HRID 931696 reaction equation
NC1[N:7]=[C:6](Cl)[CH:5]=[C:4](Cl)N=1.[NH2:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([O:18][CH3:19])[N:12]=1.C[O-].[Na+].[CH3:23][C:24]([CH3:26])=O>CO>[NH2:10][C:11]1[N:16]=[C:15]([NH:7][C:6]2[CH:5]=[CH:4][CH:26]=[CH:24][CH:23]=2)[CH:14]=[C:13]([O:18][CH3:19])[N:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 655222-Amino-4,6-dichloropyrimidine2×HCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-HCID 10942334Sodium Methoxide

Product 1

HCID 86698312HCID 86698312, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

2-Amino-4-anilino-6-methoxypyrimidine was synthesized using 2-amino-4,6-dichloropyrimidine as a starting material through 2-amino-4-chloro-6-methoxypyrimidine. A solution of sodium methoxide in 28% methanol (43 mL) at an internal temperature of 20° C. or less was dropwise added to a mixture of 2-amino-4,6-dichloropyrimidine (32.8 g) and acetone (700 mL) under ice cooling. The reaction was further continued at an internal temperature of 40° C. for 4 hours, and the solution was concentrated under reduced pressure, followed by addition of 500 mL of water. The precipitated solid was collected by filtration and was used without purification for the subsequent step. The crude product of 2-amino-4-chloro-6-methoxypyrimidine, aniline (26.7 mL), methoxyethanol (150 mL), and hydrochloric acid (0.2 mL) were mixed, followed by stirring with heating at 120° C. for 3 hours. After cooling, the reaction solution was added to aqueous sodium bicarbonate (500 mL)/ethyl acetate under ice cooling to extract the product with ethyl acetate. After the concentration, purification by column chromatography (ethyl acetate/n-hexane) was performed to yield 14 g of 2-amino-4-anilino-6-methoxypyrimidine.

Workup

  1. custom2-Amino-4-anilino-6-methoxypyrimidine was synthesized
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionfollowed by addition of 500 mL of water
  4. filtrationThe precipitated solid was collected by filtration
  5. customwas used without purification for the subsequent step
  6. additionThe crude product of 2-amino-4-chloro-6-methoxypyrimidine, aniline (26.7 mL), methoxyethanol (150 mL), and hydrochloric acid (0.2 mL) were mixed
  7. temperatureAfter cooling
  8. additionthe reaction solution was added to aqueous sodium bicarbonate (500 mL)/ethyl acetate under ice cooling
  9. extractionto extract the product with ethyl acetate
  10. concentrationAfter the concentration, purification by column chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e23d9bc08be74c808dd38efdb55b518d
Source dataset
uspto-grants-2016_03
Patent number
US09296877B2

Reaction notes

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