5-Bromopyrimidine → HCID 67350934, compound

HRID 1672769Notes

Reaction equation

HRID 1672769 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:25]=1)[CH3:2].Br[C:27]1[CH:28]=[N:29][CH:30]=[N:31][CH:32]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(O)(C)(C)C>[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:27]4[CH:28]=[N:29][CH:30]=[N:31][CH:32]=4)[CH2:23][CH2:24]3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:25]=1)[CH3:2]

Participants

8

Reactant 4

HCID 783445-BromopyrimidineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 25127534HCID 25127534, compound

Product 1

HCID 67350934HCID 67350934, compoundYield 39.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-9-Ethylamino-5-(piperidin-4-yl)methyl-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (83.6 mg, 0.243 mmol) obtained in Step 1, 5-bromopyrimidine (96.4 mg, 0.607 mmol), tris(dibenzylideneacetone)dipalladium (33.3 mg, 0.0364 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (57.4 mg, 0.146 mmol), and sodium tert-butoxide (46.6 mg, 0.485 mmol) were dissolved in 1,4-dioxane (2.8 ml) and tert-butyl alcohol (1.4 ml) under an atmosphere of nitrogen, and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was filtered through sellite, and the residue obtained by concentrating the filtrate was purified by silica gel column chromatography, and crystallized from diisopropylether to give the title compound (Compound 32) (40.2 mg, 39%).

Workup

  1. filtrationThe reaction mixture was filtered through sellite
  2. customthe residue obtained
  3. concentrationby concentrating the filtrate
  4. customwas purified by silica gel column chromatography
  5. customcrystallized from diisopropylether

Sources & evidence

ORD record
ord-a015898c79a94161878e90e25b5460d5
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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