Guanidine Hydrochloride → 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine

HRID 34462

반응식

HRID 34462 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH2:13][C:14](=[CH:17]N2CCOCC2)[C:15]#[N:16])[C:6]2[CH:7]=[CH:8][CH2:9][O:10][C:5]=2[C:4]=1[O:24][CH3:25].Cl.NC1C=CC=CC=1.Cl.[NH2:35][C:36]([NH2:38])=[NH:37].C[O-].[Na+]>>[NH2:37][C:36]1[N:38]=[C:15]([NH2:16])[C:14]([CH2:13][C:11]2[C:6]3[CH:7]=[CH:8][CH2:9][O:10][C:5]=3[C:4]([O:24][CH3:25])=[C:3]([O:2][CH3:1])[CH:12]=2)=[CH:17][N:35]=1

참가 물질

5

반응물 4

HCID 5742Guanidine HydrochlorideHCID 8870Benzenamine hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 542807632-(7,8-Dimethoxy-2H-1-benzopyran-5-ylmethyl)-3-morpholino acrylonitrile

생성물 1

HCID 128497722,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine수율 42.7%

실험 절차

2-(7,8-Dimethoxy-2H-1-benzopyran-5-ylmethyl)-3-morpholino acrylonitrile (562 g, 1.64 mol) and aniline hydrochloride (234 g, 1.80 mol) were refluxed in SD3A (2.4 L) for one hour. The reaction was cooled, and guanidine hydrochloride (313 g, 3.28 mol) and sodium methoxide (275 g, 5.08 mol) were added. After continued reflux, the product crystallized from the cooled reaction mixture. Filtration followed by water wash (2 L) gave 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine (220 g, 42.7%). Crystallization from ethanol-water gave title compound, mp 235°-238°, identical to the product of Example 1C.

후처리

  1. temperatureThe reaction was cooled
  2. temperatureAfter continued reflux
  3. customthe product crystallized from the cooled reaction mixture
  4. filtrationFiltration
  5. washwash (2 L)

출처 및 근거

ORD 기록
ord-cee52d64b5dc4625a65ee23e86a5187e
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761475

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