Dimethylformamide → N'-(2-Amino-4,6-dichloro-5-pyrimidinyl)-N,N-dimethylmethanimidamide

HRID 1080858Notes

Reaction equation

[ClH:1].[NH2:2][C:3]1[C:4](O)=[N:5][C:6]([NH2:10])=[N:7][C:8]=1O.P(Cl)(Cl)([Cl:14])=O.[CH3:17][N:18]([CH3:21])[CH:19]=O.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:4]1[C:3]([N:2]=[CH:17][N:18]([CH3:21])[CH3:19])=[C:8]([Cl:14])[N:7]=[C:6]([NH2:10])[N:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 4.46 g (25 mmol) of diaminodihydroxypyrimidine hydrochloride in 90 ml of toluene and 15.33 g (100 mmol) of phosphorus oxychloride was heated to 80° C. 7.31 g (100 mmol) of dimethylformamide was added drop-wise within a span of 60 minutes. The reaction mixture was then stirred at 80° C. for 16 hours. It was allowed to cool down, and 100 ml of water was then added. The pH was adjusted to 10 using a total of 8.4 g of Na2CO3. The reaction mixture was heated to 40° C. and stirred at this temperature for 4 hours. It was then cooled down to room temperature and neutralized with a 30% solution of NaOH, and the product was filtered off. After washing with water and drying in vacuo, 5.5 g (95%) of product was obtained as a beige solid. This corresponds to a yield of 89%.

Workup

temperatureto cool down
temperatureThe reaction mixture was heated to 40° C.
stirringstirred at this temperature for 4 hours
temperatureIt was then cooled down to room temperature
filtrationthe product was filtered off
washAfter washing with water
customdrying in vacuo

Sources & evidence

ORD record: ord-658c42aeb0104a0ab37344691383fad4
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583226

Reaction notes

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