5-Bromopyrimidine → HCID 23119574, compound

HRID 724952Notes

Reaction equation

C([N:3]1[C:9]2[N:10]=[CH:11][C:12](C#C)=[CH:13][C:8]=2[C:7](=[O:16])[N:6](C)[C:5]2[CH:18]=[CH:19][CH:20]=[N:21][C:4]1=2)C.BrC1C=NC=NC=1>>[N:21]1[C:4]2[C:5](=[N:6][C:7](=[O:16])[C:8]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]=3[N:3]=2)[CH:18]=[CH:19][CH:20]=1

Participants

Reactant 2

HCID 783445-Bromopyrimidine

HCID 10802535HCID 10802535, compound

Product 1

HCID 23119574HCID 23119574, compoundYield 85.9%

Procedure

By a procedure analogous to that described in Example 51b, 5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.1 g, 0.36 mmol) was coupled with 5-bromopyrimidine (59 mg, 0.37 mmol) to give 65 mg of 5,11-Dihydro-11-ethyl-5-methyl-8-(5-pyrimidyl)ethynyl-(-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (65 mg). A mixture containing this coupled product (65 mg), cyclohexene (0.07 mL), and 10% palladium on carbon (60 mg) in 2 mL of ethanol was heated in a sealed tube at 95° C. for 5 hours. The reaction mixture was filtered through Celite and concentrated. Purification of the residue by flash chromatography, eluting with methanol/dichloromethane, and recrystallization from ethyl acetate/hexanes provided 27 mg of the title compound, m.p. 142°-143° C.

Sources & evidence

ORD record: ord-dde71374fcc04796bc3fe6a40657542c
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705499

Reaction notes

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