Ammonium Chloride → HCID 86713570, compound

HRID 2404025Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:33]=[N:32][C:16]2[N:17]=[C:18]([NH:21][C:22]3[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:31])[N:19]=[CH:20][C:15]=2[CH:14]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:33]=[N:32][C:16]2[N:17]=[C:18]([NH:21][C:22]3[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:31])[N:19]=[CH:20][C:15]=2[CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)pyrido[2,3-d]pyrimidin-2-amine (80 mg, 0.168 mmol) in ethanol (4 mL) and water (4 mL) was added iron powder (75 mg, 1.344 mmol) and ammonium chloride (74 mg, 1.344 mmol). The mixture was stirred at 100° C. for 2 hrs, cooled to RT, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1) to afford N1-(6-(2,6-dichloro-3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-yl)-6-methylbenzene-1,2-diamine (40 mg, 53%) as a yellow solid. MS (ES+) C22H19Cl2N5O2 requires: 455, 457. found: 456, 458 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.33 (br. s., 1H), 9.01 (s, 1H), 9.65 (br. s., 1H), 8.23 (s, 1H), 7.05 (s, 1H), 6.93 (br. s., 1H), 6.64-6.63 (m, 1H), 6.50-6.49 (m, 1H), 4.80 (s, 2H), 3.99 (s, 6H), 2.09 (s, 3H).

Workup

temperaturecooled to RT
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1)

Sources & evidence

ORD record: ord-9db996bee0ff47fb97fb2926f0830784
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802697B2

Reaction notes

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