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

HRID 34467

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].NC(N)=N.[CH3:13][O:14][C:15]1[CH:24]=[C:23]([CH:25]=[C:26]([CH2:29]OC)[C:27]#[N:28])[C:18]2[CH:19]=[CH:20][CH2:21][O:22][C:17]=2[C:16]=1[O:32][CH3:33]>CO>[NH2:4][C:3]1[N:5]=[C:27]([NH2:28])[C:26]([CH2:25][C:23]2[C:18]3[CH:19]=[CH:20][CH2:21][O:22][C:17]=3[C:16]([O:32][CH3:33])=[C:15]([O:14][CH3:13])[CH:24]=2)=[CH:29][N:2]=1

Participants

Conditions

Temperature: 3 °C

Procedure

Guanidine hydrochloride (11.46 g, 0.12 mole) in methanol (25 mL) was added to sodium methoxide (6.55 g, 0.12 mole) in methanol (40 mL) and the resultant sodium chloride was filtered and washed with methanol (10 mL). The guanidine solution was added to 3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile (11.5 g, 0.04 mole) and the mixture heated at reflux for 2 hr. Cooling the mixture at 3° C. provided 5.38 g of yellow solid in two crops. HPLC assayed yield of 28.6%. A sample recrystallized from alcohol/water gave mp 232°-4° C.

Workup

filtrationthe resultant sodium chloride was filtered
washwashed with methanol (10 mL)
temperaturethe mixture heated
temperatureat reflux for 2 hr

Sources & evidence

ORD record: ord-817e59b075864a43ba1165743bca3c56
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04761475

Linked notes

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