Cesium carbonate → HCID 69669181, compound

HRID 450566Notes

Reaction equation

HRID 450566 reaction equation
[NH2:1][C:2]1[C:3]([O:8][CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:21]1[C:22]2[C:29]([CH3:30])=[C:28]([C:31]([O:33][CH3:34])=[O:32])[S:27][C:23]=2N=CN=1.[CH3:35][C:36]1(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=C[C:37]1=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]>[CH3:34][O:33][C:31]([C:28]1[S:27][C:23]2[CH:35]=[CH:36][CH:37]=[C:21]([NH:1][C:2]3[C:3]([O:8][CH:9]4[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]4)=[N:4][CH:5]=[CH:6][CH:7]=3)[C:22]=2[C:29]=1[CH3:30])=[O:32]

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 696690941211758-73-4

Product 1

HCID 69669181HCID 69669181, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

Tert-butyl 3-(3-aminopyridin-2-yloxy)azetidine-1-carboxylate (1.56 g, 5.90 mmol) was added into a solution of methyl 4-chloro-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (1.57 g, 6.49 mmol), XANTPHOS (0.683 g, 1.18 mmol) and cesium carbonate (2.69 g, 8.26 mmol) in degassed 1,4-dioxane (50 mL). The mixture was degassed under sonnication, tris(dibenzylideneacetone)dipalladium (0.270 g, 0.30 mmol) added and the mixture sonnicated further. The reaction was sealed, heated at 90° C. overnight and concentrated in vacuo. The product was purified by flash-column chromatography (petroleum ether (40-60° C.) 1:1 petroleum ether (40-60° C.)/EtOAc), trituration from MeCN and reverse phase preparative HPLC to yield the title compound as yellow solid.

Workup

  1. additionadded
  2. customThe reaction was sealed
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by flash-column chromatography (petroleum ether (40-60° C.) 1:1 petroleum ether (40-60° C.)/EtOAc), trituration from MeCN

Sources & evidence

ORD record
ord-2604951657f14205a91ba12bfd4c5c17
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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