Sodium ethoxide → (7-benzyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-2-yl)-phenyl-amine

HRID 400465Notes

Reaction equation

Cl.[CH2:2]([N:9]1[CH2:15][CH2:14][C:13](Cl)=[C:12]([CH:17]=O)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]([NH2:28])[NH2:27])=[CH:21][CH:20]=1.C(O)(O)=O.C([O-])C.[Na+]>C(O)C>[CH2:2]([N:9]1[CH2:10][CH2:11][C:12]2[CH:17]=[N:27][C:26]([NH:25][C:22]3[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=3)=[N:28][C:13]=2[CH2:14][CH2:15]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1 g 1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde hydrochloride was added to 1 g phenylguanidine carbonate salt and 1 g sodium ethanolate in 25 mL ethanol. The reaction was stirred 4 h at 70° C. The mixture was filtered over silica gel and the solvent was removed. The residue was purified by chromatography on silica gel (dichlormethane/MeOH/ammonia: 19/1/0.1) to yield 300 mg of the desired product.

Workup

filtrationThe mixture was filtered over silica gel
customthe solvent was removed
customThe residue was purified by chromatography on silica gel (dichlormethane/MeOH/ammonia: 19/1/0.1)

Sources & evidence

ORD record: ord-afee4ea0a0fa4078a729b243170162ac
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741892B2

Reaction notes

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