Hydrochloric Acid → HCID 178490296, compound

HRID 1463267Notes

Reaction equation

[OH:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[C:6]([OH:16])[N:5]=[C:4](SC)[N:3]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26][NH2:27])=[CH:23][CH:22]=1.Cl>O>[OH:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[C:6]([OH:16])[N:5]=[C:4]([NH:27][CH2:26][CH2:25][C:24]2[CH:28]=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4,6-dihydroxy-5-(2-furanylcarbonyl)amino-2-methylthiopyrimidine (2 g, 7.5 mM), p-methoxyphenethylamine (3.4 g, 22.5 mM), and water (25 ml) was heated at 90° C. for 15 hours. The mixture was then poured into water (100 ml) and acidified with concentrated hydrochloric acid until PH<3. The resultant precipitate was removed by filtration and recrystallised from methanol/water (3:1) to afford 4,6-dihydroxy-5-(2-furanylcarbonyl)amino-2-[(4-methoxyphenyl)ethyl]aminopyrimidine as a white solid (0.46 g, 16.6% yield) m.p. >250° C.; NMR: DMSO-d6 : 2.75(t, 2H, ArCH2), 3.47(brq, 2H, CH2NH), 3.73(s, 3H, OMe), 6.50(brs, 1H, NH), 6.61(m, 1H, furyl-H), 6.87(d, 2H, ArH), 7.16(d, 2H, ArH), 7.17(s, 1H furyl-H), 7.82(d, 1H, furyl-H), 8.64(brs, 1H, NHCO), 10.58(brs, 2H, OH×2); m/e [M+H]+, 371:

Workup

customThe resultant precipitate was removed by filtration
customrecrystallised from methanol/water (3:1)

Sources & evidence

ORD record: ord-9b9c4291ffc0427bbabdab22046362fc
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05300509

Reaction notes

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