Water → HCID 69884992, compound

HRID 1836109Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CS([C:22]1[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2/[C:35](=[CH:40]\[O:41][CH3:42])/[C:36]([O:38][CH3:39])=[O:37])[CH:23]=1)(=O)=O.O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:22]2[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3/[C:35](=[CH:40]\[O:41][CH3:42])/[C:36]([O:38][CH3:39])=[O:37])[CH:23]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-nitrobenzyl alcohol (666 mg) in DMF (8 ml) was added potassium carbonate (800 mg) followed by a solution of (E)-methyl 2-[2-(6-methanesulphonylpyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.0 g, prepared as described in Example 1) in DMF (3 ml). The reaction mixture was heated to 60° C. under an atmosphere of nitrogen for 5½ hours, cooled and then poured into water (40 ml). The resulting mixture was extracted with ether (×3) and the combined ether layers were dried and evaporated to yield an orange oil. Chromatography (eluent ether-hexane, 7:3) gave (E)-methyl 2-[2-(6-(4-nitrobenzyloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (532 mg) as a glass which solidified on standing; m.p. 96-98° C.; 1H NMR: δ 3.55 (3H, s), 3.75 (3H, s), 5.50 (2H, s), 6.15 (1H, s), 7.15 (1H, d), 7.3 (3H, m), 7.45 (1H, s), 7.58 (2H, d), 8.22 (2H, d), 8.42 (1H, s) ppm; IR maxima: 1700, 1620, 1560, 1340 cm−1; mass spectrum m/e 437 (M+).

Workup

temperaturecooled
extractionThe resulting mixture was extracted with ether (×3)
dry with materialthe combined ether layers were dried
customevaporated
customto yield an orange oil

Sources & evidence

ORD record: ord-b636c8577e494adbb97fd567beeab743
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777412B2

Reaction notes

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