Dimethylformamide → HCID 123555910, compound

HRID 882129Notes

Reaction equation

Br[C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]([C:13]3[C:14]4[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:19]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:15]=4[N:16]=[CH:17][N:18]=3)[CH:10]=[CH:11][CH:12]=2)[S:4][N:3]=1.[CH3:35][N:36](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:35]([C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]([C:13]3[C:14]4[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:19]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:15]=4[N:16]=[CH:17][N:18]=3)[CH:10]=[CH:11][CH:12]=2)[S:4][N:3]=1)#[N:36]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of ethyl 4-(3-(3-bromo-1,2,4-thiadiazol-5-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (51 mg, 0.092 mmol), tetrakis(triphenylphosphine)palladium(0) (53 mg, 0.046 mmol), and zinc cyanide (107 mg, 0.915 mmol) in DMF (1.0 mL) was heated to 95° C. overnight. The resulting mixture was filtered and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-50% ethyl acetatehexane gave ethyl 4-(3-(3-cyano-1,2,4-thiadiazol-5-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C24H27N6O3SSi [M+H]+: 507, found 507.

Workup

filtrationThe resulting mixture was filtered
concentrationconcentrated under reduced pressure
customPurification by chromatography on silica eluting with 0-50% ethyl acetatehexane

Sources & evidence

ORD record: ord-9f6471692d8e4a68a38254fd745491e7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993756B2

Reaction notes

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