Ethanol → 2-Amino-4-anilino-6-methylaminopyrimidine

HRID 931697노트

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HRID 931697 반응식
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([NH:9][CH3:10])[N:3]=1.NC1[N:17]=[C:16](Cl)[CH:15]=[C:14](Cl)N=1.[CH3:20]N.[CH2:22](O)[CH3:23]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:17][C:16]2[CH:15]=[CH:14][CH:23]=[CH:22][CH:20]=2)[CH:5]=[C:4]([NH:9][CH3:10])[N:3]=1

참가 물질

5

반응물 4

HCID 702EthanolHCID 6329MethylamineHCID 655222-Amino-4,6-dichloropyrimidine2회HCID 2354466-Chloro-n4-methylpyrimidine-2,4-diamine

생성물 1

HCID 807680532-Amino-4-anilino-6-methylaminopyrimidine

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온도
70 °C

실험 절차

2-Amino-4-anilino-6-methylaminopyrimidine was synthesized, via 2-amino-4-chloro-6-methylaminopyrimidine, with 2-amino-4,6-dichloropyrimidine as a starting material. 2-Amino-4,6-dichloropyrimidine (32.8 g), a 40% aqueous methylamine solution (34.5 mL), and ethanol (300 mL) were mixed, followed by stirring at an internal temperature of 70° C. for 4 hours. Subsequently, the solvent was concentrated under reduced pressure, and crystallization from acetonitrile was performed. The product was collected by filtration and was used without purification for the subsequent step. The crude product of 2-amino-4-chloro-6-methylaminopyrimidine, aniline (27.4 mL), methoxyethanol (100 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 sodium bicarbonate water (500 mL)/ethyl acetate under ice cooling to extract the product with ethyl acetate. After concentration, purification by column chromatography (ethyl acetate/methanol) was performed to yield 18 g of 2-amino-4-anilino-6-methylaminopyrimidine. Synthesis was performed as in Synthetic example 1a-1 with 2-amino-4-anilino-6-methylaminopyrimidine, methyl m-methylbenzoate, and sodium methoxide. The product was purified by silica gel column chromatography using ethyl acetate/n-hexane and recrystallization from ethyl acetate/n-hexane to yield compound (6-14).

후처리

  1. concentrationSubsequently, the solvent was concentrated under reduced pressure, and crystallization from acetonitrile
  2. filtrationThe product was collected by filtration
  3. customwas used without purification for the subsequent step
  4. additionThe crude product of 2-amino-4-chloro-6-methylaminopyrimidine, aniline (27.4 mL), methoxyethanol (100 mL), and hydrochloric acid (0.2 mL) were mixed
  5. stirringby stirring
  6. temperaturewith heating at 120° C. for 3 hours
  7. temperatureAfter cooling
  8. additionthe reaction solution was added to sodium bicarbonate water (500 mL)/ethyl acetate under ice cooling
  9. extractionto extract the product with ethyl acetate
  10. concentrationAfter concentration, purification by column chromatography (ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-0d0d9d0435ef49dc965ba775ff927d5f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296877B2

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