Cesium carbonate → HCID 58413283, compound

HRID 450562Notes

Reaction equation

HRID 450562 reaction equation
[CH:1]([O:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].Cl[C:13]1[C:14]2[C:21]([CH3:22])=[C:20]([C:23]([O:25][CH3:26])=[O:24])[S:19][C:15]=2[N:16]=[CH:17][N:18]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[CH:1]([O:4][C:5]1[C:10]([NH:11][C:13]2[C:14]3[C:21]([CH3:22])=[C:20]([C:23]([O:25][CH3:26])=[O:24])[S:19][C:15]=3[N:16]=[CH:17][N:18]=2)=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 218508472-isopropoxypyridin-3-amine

Product 1

HCID 58413283HCID 58413283, compoundYield 66.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

iso-Propoxypyridin-3-amine (1.30 g, 8.60 mmol) was added into a solution of methyl 4-chloro-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (2.295 g, 9.46 mmol), XANTPHOS (0.995 g, 1.72 mmol) and cesium carbonate (3.922 g, 12.04 mmol) in degassed 1,4-dioxane (40 mL). The mixture was degassed under sonnication, tris(dibenzylideneacetone)dipalladium (0.394 g, 0.430 mmol) added and the mixture sonnicated further. The reaction was sealed, heated at 90° C. for 3.0 hours, cooled, filtered and the solid washed with cold 1,4-dioxane. The filtrate was poured into ammonium hydroxide solution and the precipitate collected to yield the title compound as dark yellow solid (2.05 g, 66%).

Workup

  1. additionadded
  2. customThe reaction was sealed
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe solid washed with cold 1,4-dioxane
  6. additionThe filtrate was poured into ammonium hydroxide solution
  7. customthe precipitate collected

Sources & evidence

ORD record
ord-de0e3fdd32bd4970af38d872c307fbb3
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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