Formic Acid → HCID 16638380, compound

HRID 1087039Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:13])=[N:4][C:5]([NH:9][C:10](=[O:12])[CH3:11])=[N:6][C:7]=1[Cl:8].[CH:14](O)=[O:15]>C(OC(=O)C)(=O)C>[Cl:8][C:7]1[C:2]([NH:1][CH:14]=[O:15])=[C:3]([Cl:13])[N:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[N:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

N-(5-Amino-4,6-dichloropyrimidin-2-yl)acetamide (J. Org. Chem. 1975, 40, 3141) was formylated by addition of 96% formic acid (20 mL) to a solution of (0.75 g, 3.4 mmoles) dissolved in acetic anhydride (20 mL). The resulting solution was stirred at 25° C. for one hour and then evaporated to give N-(4,6-dichloro-5-formamido-2-pyrimidinyl)acetamide as tan powder (0.77 g, 91%); structure confirmed by 1H-NMR and mass spectrum. This tan powder (840 mg, 3.37 mmol), (±)-cis-4-amino-2-cyclopentene-1-methanol (940 mg, 8.2 mmol), and triethylamine (0.80 g, 8.0 mmol) were warmed in ethanol (50 mL) in an oil bath (70°-80° C.) under nitrogen for 50 minutes and evaporated to a dark oil which was chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform as a peach-colored solid foam (840 mg). Crystallization from methanol gave white granules (575 mg, 52%); m.p. 189°-193°; 1H-NMR (DMSO-d6) δ10.23 (br, 1.0, NHAc), 9.3 (br, 1.0, NHCHO), 8.15 and 7.90 (both s, total 1.0, HC=O from two conformers, peaks coalesce at 60° C.), 7.42 and 7.22 (both d, J=8.3, total 1.0, CH--NH from two conformers, peaks coalesce at 60° C.), 5.9 and 5.7 (both m, 2.0, CH=CH), 5.05 (m, 1, CH--N), 4.73 (m, 1, OH), 3.39 (m, 2, CH2OH), 2.72 (m, 1, CH), 2.40 (m, 1, 1/2CH2), 1.36 (m, 1, 1/2CH2).

Workup

customevaporated

Sources & evidence

ORD record: ord-c9526c52c9cc4111aab281bc976b414d
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034394

Reaction notes

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