Sodium hydride → HCID 178525914, compound

HRID 2410021Notes

Reaction equation

[OH:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[C:6](=[O:17])[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4](=[O:25])[C:3]=1[C:26](OCC)=[O:27].C1(CNC([CH:41](C(OCC)=O)[C:42]([O:44]CC)=[O:43])=O)C=CC=CC=1.[H-].[Na+].[N+:54](C1C=CC=CC=1N=C=O)([O-])=O>O1CCOCC1.ClCCl>[OH:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[C:6](=[O:17])[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4](=[O:25])[C:3]=1[C:26]([NH:54][CH2:41][C:42]([OH:44])=[O:43])=[O:27]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 6-hydroxy-1-(2-nitrophenyl)-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate. Diethyl {[(phenylmethyl)amino]carbonyl}propanedioate (420 mg, 1.43 mmoles) was added to a suspension of sodium hydride (60% suspension in mineral oil, 220 mg, 5.5 mmoles) in dry dioxan (10 mL) and stirred for 10 minutes under argon. 2-Nitrophenyl isocyanate (360 mg, 2.20 mmoles) was added and the mixture sealed in a pressure flask heated in a microwave reactor at 110° C. for 1 hour. The mixture was taken up in dichloromethane, washed with 1 molar hydrochloric acid and evaporated onto silica gel. Flash chromatography (hexane to 0.5% formic acid in ethyl acetate) gave the title compound (59 mg, 7%) 1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (s, 1 H), 7.81 (s, 1 H), 7.68 (s, 1 H), 7.47 (s, 1 H), 7.08-7.38 (m, 5 H), 4.77-5.16 (m, 2 H), 4.12 (q, J=5.31 Hz, 2 H), 0.97-1.31 (m, 3 H)

Workup

customthe mixture sealed in a pressure flask
washwashed with 1 molar hydrochloric acid
customevaporated onto silica gel

Sources & evidence

ORD record: ord-8fb3583deec645ce8db4effbebeecdb8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815884B2

Reaction notes

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