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

反応式

[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

参加物

反応物 4

HCID 5742Guanidine Hydrochloride

HCID 8870Benzenamine hydrochloride (1:1)

HCID 10942334Sodium Methoxide

HCID 542807632-(7,8-Dimethoxy-2H-1-benzopyran-5-ylmethyl)-3-morpholino acrylonitrile

生成物 1

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

実験手順

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.