Hydrochloric Acid → 2,4-Diamino-5-(5-amino-6-methyl-8-quinolylmethyl)pyrimidine dihydrochloride

HRID 34458

反応式

HRID 34458 の反応式
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.CC1C([N+]([O-])=O)=C2C(=CC=1)N=CC=C2.[NH2:27][C:28]1[N:33]=[C:32]([NH2:34])[C:31]([CH2:35]O)=[CH:30][N:29]=1.[ClH:37]>C(O)(=O)C>[ClH:37].[ClH:37].[NH2:27][C:28]1[N:33]=[C:32]([NH2:34])[C:31]([CH2:35][C:9]2[CH:10]=[C:11]([CH3:12])[C:2]([NH2:1])=[C:3]3[C:8]=2[N:7]=[CH:6][CH:5]=[CH:4]3)=[CH:30][N:29]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 900096-Methyl-5-nitroquinolineHCID 2958782,4-Diamino-5-pyrimidinemethanolHCID 30221825-Amino-6-methylquinoline

生成物 1

HCID 201297742,4-Diamino-5-(5-amino-6-methyl-8-quinolylmethyl)pyrimidine dihydrochloride収率 40%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 5-amino-6-methylquinoline (2.16 g, 13.7 mmol), prepared by reduction of 6-methyl-5-nitroquinoline (R. Long and K. Schofield, J. Chem. Soc. 1953, 2350), 2,4-diamino-5-hydroxymethylpyrimidine (1.91 g, 13.6 mmol), concentrated hydrochloric acid (1.9 mL), and glacial acetic acid was refluxed for 2 hr. The cooled reaction mixture was filtered and the precipitate washed with ether and dried (4.17 g). Recrystallization from aqueous ethanol with hydrochloric acid gave title compound as red-orange solid (2.08 g, 40%); mp >290° dec. Anal. Calcd for C15H16N6.2HCl.2H2O: C, 46.28; H, 5.70; N, 21.59; Cl, 18.21. Found: C, 46.13; H, 5.61; N, 21.66; Cl, 18.25.

後処理

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe precipitate washed with ether
  4. customdried (4.17 g)
  5. customRecrystallization from aqueous ethanol with hydrochloric acid

出典と根拠

ORDレコード
ord-a4b240709c5e49b4b1bd1b4880b43784
出典データセット
uspto-grants-1988_08
特許番号
US04761475

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