Triethylamine → HCID 178461601, compound

HRID 522809Notes

Reaction equation

HRID 522809 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:7]=[C:6]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]1[CH3:24])[N:5]=2.[NH:25]1[CH:29]=[CH:28][C:27](B(O)O)=[N:26]1.CCN(CC)CC>C(COC)OC.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:24][C@H:19]1[CH2:20][O:21][CH2:22][CH2:23][N:18]1[C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([C:29]3[CH:28]=[CH:27][NH:26][N:25]=3)[NH:3]2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:7]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 178461599HCID 178461599, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 178461601HCID 178461601, compoundYield 39.2%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

8-Bromo-2-((S)-3-methyl-morpholin-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (50 mg, 126 μmol) was dissolved in dimethoxyethane (2 mL) and water (0.2 mL), followed by addition of 1H-pyrazole-3-ylboronic acid (21.1 mg, 189 μmol), PdCl2(dppf) (9.21 mg, 13 μmol) and NEt3 (53 μl, 378 μmol) under argon. The reaction mixture was heated to 85° C. for 23 hours. The reaction mixture was then diluted with EtOAc, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (12 g SiO2, EtOAc) to give the product (19 mg, 39% yield).

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (12 g SiO2, EtOAc)

Sources & evidence

ORD record
ord-8445d1de8ad647769629ef46a8d250aa
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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