4-Bromopyrimidine-2-carbonitrile → Ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882127Notes

Reaction equation

HRID 882127 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]3[C:16]4[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][N:21]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[CH:13][CH:14]=2)O1.Br[C:39]1[CH:44]=[CH:43][N:42]=[C:41]([C:45]#[N:46])[N:40]=1>C(=O)([O-])[O-].[Na+].[Na+].COCCOC.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:45]([C:41]1[N:42]=[C:43]([C:9]2[CH:10]=[C:11]([C:15]3[C:16]4[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][N:21]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[CH:13][CH:14]=2)[CH:44]=[CH:39][N:40]=1)#[N:46]

Participants

6

Reactant 2

HCID 534079104-Bromopyrimidine-2-carbonitrileHCID 89629877HCID 89629877, compound

Product 1

HCID 89630128Ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of ethyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (54.4 mg, 0.104 mmol), 4-bromopyrimidine-2-carbonitrile (38.2 mg, 0.208 mmol), and tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.021 mmol) in 2 M aqueous sodium carbonate (150 uL) and DME (500 μL) was purged with argon. The reaction vessel was then sealed and heated at 95° C. overnight. The reaction mixture was filtered through Celite and rinsed with ethyl acetate. The reaction solution was concentrated under reduced pressure and the residue purified by chromatography on silica eluting with 40-60% ethyl acetatehexane to give the desired product. LRMS calc'd for C26H29N6O3Si [M+H]+: 501, found 501.

Workup

  1. customwas purged with argon
  2. customThe reaction vessel was then sealed
  3. filtrationThe reaction mixture was filtered through Celite
  4. washrinsed with ethyl acetate
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue purified by chromatography on silica eluting with 40-60% ethyl acetatehexane

Sources & evidence

ORD record
ord-52b0886f08984b8583dca5ffd52fcb58
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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