Hydrochloric Acid → 5-(Benzyloxy)-2-methoxy-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

HRID 1754255Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[NH:13][C:12]([O:16][CH3:17])=[N:11][C:10]=1[C:18]([O:20]C(C)(C)C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[NH:13][C:12]([O:16][CH3:17])=[N:11][C:10]=1[C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of Compound 46d (1.1 g, 3.2 mmol) in MeOH (20 mL) and THF (20 mL) was added 7 N NaOH (4.0 mL, 28 mmol) and the solution stirred at 50° C. for 3 h. The reaction mixture was cooled in an ice bath then acidified by the addition of 1 N HCl (20 mL). The resulting precipitate was filtered, rinsed with water then dried under vacuum to give Compound 46a (790 mg, 89% yield) as a white solid. LCMS ESI 277.0 (M+H), RT=1.41 min (Method Q). 1H NMR (400 MHz, DMSO-d6) δ 13.49 (br. s., 1H), 12.91 (br. s., 1H), 7.90-6.67 (m, 5H), 5.01 (s, 2H), 3.86 (s, 3H).

Workup

temperatureThe reaction mixture was cooled in an ice bath
filtrationThe resulting precipitate was filtered
washrinsed with water
customthen dried under vacuum

Sources & evidence

ORD record: ord-811d51ab1187460b92506a0ec40a6928
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169240B2

Reaction notes

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