Guanidine Hydrochloride → 2,4-Diaminopyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 4448

反応式

HRID 4448 の反応式
[NH2:1][C:2]([NH2:4])=[NH:3].Cl.C[O-].[Na+].N[C:10]1[C:15]([C:16]#[N:17])=[CH:14][C:13]([C:18]#[N:19])=[CH:12][N:11]=1.C1CCCCC1.CCOC(C)=O>CCO>[NH2:3][C:2]1[N:4]=[C:16]([NH2:17])[C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[N:11][C:10]=2[N:1]=1

参加物

6

反応物 4

HCID 5742Guanidine HydrochlorideHCID 2959122-Aminopyridine-3,5-dicarbonitrileHCID 10942334Sodium MethoxideHCID 21867204Cyclohexane ethylacetate

生成物 1

HCID 3013972,4-Diaminopyrido[2,3-d]pyrimidine-6-carbonitrile収率 95%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Guanidine·HCl (2.66 g, 27.8 mmol) was added to a solution of NaOMe (sodium methoxide) (1.50 g, 27.8 mmol) in absolute EtOH (180 mL). The mixture was stirred at 20°-23° C. for 15 minutes before 5 (2.00 g, 13.9 mmol) was added. After a 24-hour reflux period with rapid stirring, TLC (cyclohexane-EtOAc, 1:1) showed absence of 5. The solid filtered from the cooled mixture was washed on the funnel with H2O and EtOH; yield 95% (2.45 g). A sample of this material (1.0 g) was stirred with near-boiling Me2SO (dimethyl sulfoxide) (250 mL), and the slightly cloudy solution was filtered (Celite) to give a clear, pale-yellow filtrate which was then concentrated by evaporation in vacuo (to about 60 mL). Addition of EtOH (200 mL) gave 7 as a light yellow solid (880 mg); 1H NMR (Me2SO-d6) δ6.97 (2, NH2), 7.84 (s, NH2), 8.87 and 8.91 (two d, 5-H and 7-H, J=2 Hz).

後処理

  1. additionwas added
  2. filtrationThe solid filtered from the cooled mixture
  3. washwas washed on the funnel with H2O and EtOH
  4. filtrationthe slightly cloudy solution was filtered (Celite)
  5. customto give a clear, pale-yellow filtrate which
  6. concentrationwas then concentrated by evaporation in vacuo (to about 60 mL)
  7. additionAddition of EtOH (200 mL)

出典と根拠

ORDレコード
ord-01537abe3d964860950784242d6215b3
出典データセット
uspto-grants-1988_02
特許番号
US04725687

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