Ammonia → HCID 10155924, compound

HRID 1435753Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[N:3]=1.[NH3:27]>O1CCCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:6]2[N:5]=[C:4]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=3)[N:3]=[C:2]([NH2:27])[N:7]=2)[CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A pressure bottle was charged with [4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]-triazin-2-yl]-(4-dimethylaminomethyl-phenyl)-amine (0.305 g, 0.79 mmol) and tetrahydrofuran (20 ml) and cooled to −78° C. A slow stream of ammonia gas was passed into the solution for 2 minutes and the bottle was sealed. After stirring at room temperature for 12 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate to provide the title compound (0.148 g, 49% yield). 1H NMR (CDCl3) δ 7.9 (s, 1H), 7.2-7.6 (m, 6H), 3.25 (d, 6H) 2.5 (s, 3H).

Workup

customthe bottle was sealed
concentrationthe mixture was concentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate

Sources & evidence

ORD record: ord-1daa783f523c47f78ea41e69a84f5d27
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618968B2

Reaction notes

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