Cesium carbonate → HCID 68152124, compound

HRID 2047636Notes

Reaction equation

HRID 2047636 reaction equation
Br[C:2]1[C:3]([N:21]([CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([NH:26][CH3:27])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[O:19][CH3:20])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].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>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:30]1([N:21]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24](=[O:25])[N:26]([CH3:27])[C:2]3[CH:7]=[N:6][C:5]([NH:8][C:9]4[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=4[O:19][CH3:20])=[N:4][C:3]2=3)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2×HCID 67042170HCID 67042170, compound

Product 1

HCID 68152124HCID 68152124, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-(5-bromo-4-(cyclopentyl(2,2-dimethyl-3-(methylamino)-3-oxopropyl)amino)pyrimidin-2-ylamino)-3-methoxybenzoate (84 mg, 0.1572 mmol) and Cs2CO3 (74.25 mg, 0.2279 mmol) were dissolved in dioxane (2 mL) and Pd2(dba)3 (4.319 mg, 0.004716 mmol) and Xantphos (7.279 mg, 0.01258 mmol) were added. Heat to 100° C. overnight. The Xantphos and Pd2(dba)3 were replenished and the reaction heated under microwave conditions (120° C. for 30 minutes.) The solvent was removed in vacuo and the crude residue purified by column chromatography (0 to 100% EtOAc/Petrol) to give the title compound as a beige solid (42 mg, 59%); 1H NMR (400.0 MHz, DMSO) d 1.25 (s, 6H), 1.72-1.82 (m, 4H), 1.85-1.95 (m, 2H), 1.98-2.04 (m, 2H), 3.35 (s, 3H), 3.54 (s, 2H), 3.99 (s, 3H), 4.11 (s, 3H), 5.34 (quin, 1H), 7.66 (s, 1H), 7.74 (d, 1H), 7.98 (s, 1H), 8.17 (s, 1H) and 8.64 (d, 1H); MS ES(+) 454.1, ES (−) 452.1.

Workup

  1. temperaturethe reaction heated under microwave conditions (120° C. for 30 minutes.) The solvent
  2. customwas removed in vacuo
  3. customthe crude residue purified by column chromatography (0 to 100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-e5d88240b2874f2881e2b03a6dd07ddc
Source dataset
uspto-grants-2013_11
Patent number
US08592577B2

Reaction notes

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