Cesium carbonate → HCID 67258164, compound

HRID 1040018Notes

Reaction equation

HRID 1040018 reaction equation
[Si:1]([O:18][CH2:19][C:20]([C:23]1[S:24][C:25]([C:28]2[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH2:31])=[CH:26][N:27]=1)([CH3:22])[CH3:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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.Cl[C:84]1[N:89]=[C:88]([C:90]([F:93])([F:92])[F:91])[CH:87]=[CH:86][N:85]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Si:1]([O:18][CH2:19][C:20]([C:23]1[S:24][C:25]([C:28]2[CH:29]=[C:30]([NH:31][C:84]3[N:89]=[C:88]([C:90]([F:93])([F:92])[F:91])[CH:87]=[CH:86][N:85]=3)[CH:32]=[CH:33][CH:34]=2)=[CH:26][N:27]=1)([CH3:22])[CH3:21])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 67262301HCID 67262301, compound

Product 1

HCID 67258164HCID 67258164, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of the product of Step 3 (393 mg, 0.807 mmol), cesium carbonate (526 mg; 1.62 mmol), XantPhos (70.1 mg, 0.121 mmol) and palladium(II) acetate (18 mg; 0.081 mmol) in dioxane (5 mL) was added the 2-chloro-4-(trifluoromethyl)pyrimidine (102 μL; 0.848 mmol). The reaction was stirred at 100° C. overnight. After dilution with ethyl acetate (100 mL), the mixture was filtered through celite and concentrated in vacuo. Purification by chromatography on silica gel (100:0 to 50:50, hexanes:ethyl acetate) provided 327 mg (0.517 mmol, 64%) of N-{3-[2-(1-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropan-2-yl)-1,3-thiazol-5-yl]phenyl}-4-(trifluoromethyl)pyrimidin-2-amine as an off-white foam.

Workup

  1. filtrationAfter dilution with ethyl acetate (100 mL), the mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customPurification by chromatography on silica gel (100:0 to 50:50, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-b60a12e5dbad42a8a11e749ad471d7ae
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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