Cesium carbonate → Aziridin-1-yl(4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxyphenyl)methanone

HRID 529681Notes

Reaction equation

HRID 529681 reaction equation
[N:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([O:40][CH:41]4[CH2:45][CH2:44][CH2:43][CH2:42]4)[C:16]4[C:21]([C:22]5[CH:31]=[CH:30][C:25]6[N:26]=[C:27]([CH3:29])[O:28][C:24]=6[CH:23]=5)=[CH:20][N:19](COCC[Si](C)(C)C)[C:17]=4[N:18]=3)=[C:8]([O:46][CH3:47])[CH:7]=2)=[O:5])[CH2:3][CH2:2]1.ClC1N=C(OC2CCCC2)C2C(C3C=CC4N=C(C)OC=4C=3)=CN(COCC[Si](C)(C)C)C=2N=1.NC1C=CC(C(N2CC2)=O)=CC=1OC.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([O:40][CH:41]4[CH2:42][CH2:43][CH2:44][CH2:45]4)[C:16]4[C:21]([C:22]5[CH:31]=[CH:30][C:25]6[N:26]=[C:27]([CH3:29])[O:28][C:24]=6[CH:23]=5)=[CH:20][NH:19][C:17]=4[N:18]=3)=[C:8]([O:46][CH3:47])[CH:7]=2)=[O:5])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 867264206-(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazoleHCID 86726451(4-Amino-3-methoxyphenyl)(aziridin-1-yl)methanoneHCID 86726452Aziridin-1-yl(4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxyphenyl)methanone

Product 1

HCID 90293210Aziridin-1-yl(4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxyphenyl)methanone

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Aziridin-1-yl(4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxyphenyl)methanone. To a degassed mixture of 6-(2-chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv), (4-amino-3-methoxyphenyl)(aziridin-1-yl)methanone (1.2 equiv) and cesium carbonate (3 equiv) in 1,4-dioxane (0.1 M) was added palladium acetate (0.2 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.2 equiv). The reaction was stirred at 100° C. for 2 h. The reaction mixture was concentrated and the residue was purified by silica gel chromatography (0-10% DCM in methanol) to afford the title compound (crude) as a yellow solid. The material was used in next step without further purification. MS (ESI) m/z 655.1 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography (0-10% DCM in methanol)

Sources & evidence

ORD record
ord-7a13cf97da20415aa7e7a720e69d12c5
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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