Cesium carbonate → HCID 178480793, compound

HRID 577682Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:13]2[C:14]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]=3[N:16]=[C:17](Cl)[N:18]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].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.[CH3:80][N:81]1[CH:85]=[C:84]([NH2:86])[CH:83]=[N:82]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:13]2[C:14]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]=3[N:16]=[C:17]([NH:86][C:84]3[CH:83]=[N:82][N:81]([CH3:80])[CH:85]=3)[N:18]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

A microwave tube fitted with a stir bar was charged with tert-butyl((trans)-3-((2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclobutyl)carbamate (260 mg, 0.55 mmol), 1,4-dioxane (3 mL), Cs2CO3 (452 mg, 1.4 mmol), Pd2(dba)3 (16 mg, 0.03 mmol), Xantphos (34 mg, 0.056 mmol) and 1-methyl-1H-pyrazol-4-amine (60 mg, 0.58 mmol). The tube was flushed with nitrogen gas and heated at 140° C. in a Biotage microwave reactor for 40 min. The product was purified via flash chromatography eluting with a gradient of 30%-100% EtOAc in heptanes to afford the title compound (115 mg, 39% yield) as an orange foam.

Workup

customA microwave tube fitted with a stir bar
customThe tube was flushed with nitrogen gas
customThe product was purified via flash chromatography
washeluting with a gradient of 30%-100% EtOAc in heptanes

Sources & evidence

ORD record: ord-4b5e90480ad1493c87ae4de123a240c8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040547B2

Reaction notes

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