Hydrochloric Acid → 2-(2-Propoxy-5-ureidophenyl)-8-azapurin-6-one

HRID 1863133Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1.[NH2:22][C:23](N)=[O:24].Cl>O>[CH2:19]([O:18][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23]([NH2:22])=[O:24])=[CH:7][C:6]=1[C:8]1[N:16]=[C:15]2[C:11](=[N:12][N:13]=[N:14]2)[C:10](=[O:17])[N:9]=1)[CH2:20][CH3:21]

Participants

Conditions

Temperature: 175 °C

Procedure

An intimate mixture of 2-(5-amino-2-propoxyphenyl)-8-azapurin-6-one (2 g) and urea (6 g) was heated at 175° C. for one hour. The mixture was then dissolved in water (50 ml) and the solution was acidified by treatment with concentrated hydrochloric acid. The resulting suspension was heated to boiling point and filtered. The solid was dissolved in dilute aqueous ammonia solution (2 N) and this hot solution was acidified by treatment with concentrated hydrochloric acid. The cooled suspension was filtered to give 2-(2-propoxy-5-ureidophenyl)-8-azapurin-6-one (0.7 g), in the form of a microcrystalline solid, m.p. 264°-268° C. (with decomposition).

Workup

temperatureThe resulting suspension was heated
filtrationfiltered
dissolutionThe solid was dissolved in dilute aqueous ammonia solution (2 N)
filtrationThe cooled suspension was filtered

Sources & evidence

ORD record: ord-ca603a39920c432b857e44a6dbd2eb9f
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167568

Reaction notes

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