Sodium Hydroxide → HCID 118598989, compound

HRID 1050400Notes

Reaction equation

[OH-].[Na+].C(OC([NH:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]2[C:23](=[O:24])[N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:21]([C:34]([O:36]CC)=[O:35])=[C:20]([Cl:39])[CH:19]=2)[CH:12]=1)=O)(C)(C)C>CO.O1CCCC1.O>[NH2:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]2[C:23](=[O:24])[N:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[C:21]([C:34]([OH:36])=[O:35])=[C:20]([Cl:39])[CH:19]=2)[CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydroxide (0.26 g, 6.6 mmol) was added to a suspension of ethyl 5-((6-((tert-butoxycarbonyl)amino)pyrimidin-4-yl)amino)-3-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridine-2-carboxylate (0.70 g, 1.32 mmol) in methanol/tetrahydrofuran/water (2:1:1, 30 mL). The mixture was stirred at 80° C. for 16 h. After completion, the solvent was evaporated to dryness under reduced pressure. The crude was diluted with 1 N hydrochloric acid. The precipitate obtained was collected by filtration, dried, washed with pentane and dried further to afford 5-((6-aminopyrimidin-4-yl)amino)-3-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid (5) as brown solid. Yield: 0.45 g, 85%; MS (ESI) m/z 402.09 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.62 (s, 1H), 8.43 (s, 1H), 8.33 (s, 1H), 7.67 (brs, 2H), 7.19 (d, J=8.16 Hz, 2H), 6.87 (d, J=8.12 Hz, 2H), 6.39 (s, 1H), 5.18 (s, 2H), 3.71 (s, 3H).

Workup

customAfter completion, the solvent was evaporated to dryness under reduced pressure
additionThe crude was diluted with 1 N hydrochloric acid
customThe precipitate obtained
filtrationwas collected by filtration
customdried
washwashed with pentane
customdried further

Sources & evidence

ORD record: ord-3a7409c03a0a4e3392c4a7f8f0576604
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382248B2

Reaction notes

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