Ammonia → 1-[3-(7-Oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyphenyl]-3-propan-2-ylurea

HRID 1863132Notes

Reaction equation

HRID 1863132 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.[CH:22]([N:25]=[C:26]=[O:27])([CH3:24])[CH3:23].N.Cl>CN1CCCC1=O>[CH2:19]([O:18][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:26]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:27])=[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

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 61277Isopropyl isocyanateHCID 203929612-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one

Product 1

HCID 203929631-[3-(7-Oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyphenyl]-3-propan-2-ylureaYield 51.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-(5-amino-2-propoxyphenyl)-8-azapurin-6-one (1.5 g) in anhydrous N-methylpyrrolid-2-one (7 ml) was treated with isopropyl isocyanate (0.5 g). The mixture was kept at room temperature overnight and then added to dilute aqueous ammonia solution (50 ml; 2 N). The resulting solution was acidified by treatment with concentrated hydrochloric acid, and the solid which separated was crystallised from methanol to give 2-[2-propoxy-5-(3-isopropylureido)phenyl]-8-azapurin-6-one (1.0 g), in the form of colourless prisms, m.p. 203°-205° C. (with decomposition).

Workup

  1. customthe solid which separated
  2. customwas crystallised from methanol

Sources & evidence

ORD record
ord-6561d38ae08c466f94f570a33abc80cf
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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