Hydrochloric Acid → HCID 10369553, compound

HRID 2108686Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=1.Cl.C(OCC)C>CC(O)C.C(#N)C.O>[ClH:8].[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[N:4][C:5]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:27][CH:28]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 5-bromo-2-chloro-N-(3,4,5-trimethoxyphenyl)pyrimidin-4-amine (67 mg, 0.178 mmol) and N-(4-aminophenyl)acetamide (28 mg, 0.185 mmol) in 2-propanol (2 mL) was added 1N HCl in diethyl ether (50 uL, 0.05 mmol). The reaction mixture was heated at 90° C. for approx. 36 hours. After the reaction was cooled to room temperature the mixture was taken up in 1:1 acetonitrile/H2O (60 mL) and lyopholized to give N-[4-({5-bromo-4-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-2-yl}amino)phenyl]acetamide hydrochloride (67 mg, 72%) as a grey solid. 1H NMR (DMSO-d6/D2O): δ 8.21 (s, 1H), 7.25-7.67 (m, 4H), 6.87 (s, 2 H), 3.70 (s, 3 H), 3.69 (s, 6 H), 2.00 (s, 3H). MS m/z 488 (M+1).

Workup

temperatureAfter the reaction was cooled to room temperature the mixture

Sources & evidence

ORD record: ord-b44ebf7607dc4ad182c47851c891868d
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514446B2

Reaction notes

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