Lithium Bromide → Butylamine

HRID 732929Notes

Reaction equation

HRID 732929 reaction equation
N1[C:5]2=[N:6][CH:7]=N[CH:9]=[C:4]2[C:3](=O)N=1.[CH3:11][N:12](P(N(C)C)(N(C)C)=O)[CH3:13].[CH2:22]1[C:27](=O)[N:26](Br)[C:24](=[O:25])[CH2:23]1.[Li+].[Br-]>C(#N)C>[NH:6]1[CH2:5][CH2:4][O:25][CH2:24][CH2:7]1.[CH2:24]([NH2:26])[CH2:23][CH2:22][CH3:27].[NH:12]1[CH2:13][CH2:9][CH2:4][CH2:3][CH2:11]1

Participants

7

Reactant 3

HCID 82050Lithium BromideHCID 66667981HCID 66667981, compoundHCID 131727625HCID 131727625, compound

Product 3

HCID 8007ButylamineHCID 8082PiperidineHCID 8083Morpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reaction of 5 with formamide in excess at 190° C. for 8 h afforded the pyrazolo[3,4-d]pyrimidinone 10 which was purified by dissolving the crude in 2M NaOH, boiling with coal, followed by precipitation with acetic acid (yield 70%, m.p. 271-272° C.). Compound 11 was prepared in a yield of 44% following the Beal and Véliz9 procedure by treatment of 10 with a mixture of HMPT/NBS in acetonitrile at −20° C. followed by addition of LiBr and refluxing. It is interesting to point out that the secondary OH on the side chain remained unaltered by this procedure, as shown by its 1H NMR spectrum. Treatment of 11 with morpholine, butylamine, or piperidine gave the desired compounds 3a-c.

Workup

  1. temperaturerefluxing

Sources & evidence

ORD record
ord-35c628af782442409ec60162b81f8634
Source dataset
uspto-grants-2009_09
Patent number
US07589086B2

Reaction notes

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