Guanidine Hydrochloride → 2-Amino-6-(4-methoxydibenzo[b,d]furan-1-yl)-5,6,7,8-tetrahydroquinazoline-6-carbonitrile

HRID 2383984Notes

Reaction equation

CN(/[CH:4]=[C:5]1\[CH2:6][C:7]([C:14]2[C:22]3[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[O:19][C:18]=3[C:17]([O:27][CH3:28])=[CH:16][CH:15]=2)([C:12]#[N:13])[CH2:8][CH2:9][C:10]\1=O)C.Cl.[NH2:30][C:31]([NH2:33])=[NH:32].[O-]CC.[Na+]>C(O)C>[NH2:32][C:31]1[N:33]=[CH:4][C:5]2[CH2:6][C:7]([C:14]3[C:22]4[C:21]5[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=5[O:19][C:18]=4[C:17]([O:27][CH3:28])=[CH:16][CH:15]=3)([C:12]#[N:13])[CH2:8][CH2:9][C:10]=2[N:30]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of the compound obtained in example 6 (100 mg, 0.267 mmol), guanidine HCl (33.5 mg, 0.35 mmol) and sodium ethoxide (25 mg, 0.35 mmol) in 5 ml ethanol was heated at 70-80° C. for 1 hr. The mixture was cooled to room temperature and the solvent was evaporated under vacuum. The crude residue was purified by column chromatography to get 80 mg (81% yields) of a white colored solid product.

Workup

temperatureThe mixture was cooled to room temperature
customthe solvent was evaporated under vacuum
customThe crude residue was purified by column chromatography
customto get
custom80 mg (81% yields) of a white colored solid product

Sources & evidence

ORD record: ord-4feef8dbcf2e402496b1c72606782ae9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263648B2

Reaction notes

Loading…