Sodium hydride → HCID 178525916, compound

HRID 2410020Notes

Reaction equation

[OH:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6](=[O:14])[N:5]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4](=[O:22])[C:3]=1[C:23](OCC)=[O:24].[N:28](C1C=CC=CN=1)=C=O.[H-].[Na+].C1(CNC([CH:49](C(OCC)=O)[C:50]([O:52]CC)=[O:51])=O)C=CC=CC=1>O1CCOCC1.ClCCl>[OH:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6](=[O:14])[N:5]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4](=[O:22])[C:3]=1[C:23]([NH:28][CH2:49][C:50]([OH:52])=[O:51])=[O:24]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1-(2-pyridinyl)-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate. 2-Isocyanatopyridine (265 mg, 2.2 mmoles) was added to a suspension of sodium hydride (200 mg, 5 mmoles) and diethyl {[(phenylmethyl)amino]carbonyl}propanedioate (example 1a, 425 mg, 1.45 mmoles) in anhydrous dioxane (10 mL). The mixture was heated in a microwave reactor at 110° C. for 1 hour, cooled, dissolved in dichloromethane, washed with 1 molar hydrochloric acid and purified by flash chromatography (ethyl acetate-10% methanol in ethyl acetate) to give the title compound (90 mg, 12%) 1H NMR (400 MHz, DMSO-d6) δ ppm 8.93 (dd, J=7.20, 1.39 Hz, 1 H), 8.11-8.26 (m, 1 H), 7.19-7.45 (m, 7 H), 4.78-5.01 (m, 2 H), 4.15 (q, J=7.24 Hz, 2 H), 1.24 (t, J=7.07 Hz, 3 H).

Workup

temperaturecooled
washwashed with 1 molar hydrochloric acid
custompurified by flash chromatography (ethyl acetate-10% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-7d689e4d1fdc4911a0eef6c43555053d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815884B2

Reaction notes

Loading…