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

HRID 4448

반응식

HRID 4448 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-01537abe3d964860950784242d6215b3
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725687

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