Triphenylarsine → tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]ethyl]carbamate

HRID 1775299Notes

Reaction equation

HRID 1775299 reaction equation
Br[C:2]1[C:3]([NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:39]([O:41][CH:42]([O:45][CH2:46][CH3:47])[C:43]#[CH:44])[CH3:40].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1.C(N(CC)CC)C>[Cl:8][C:5]1[N:4]=[C:3]([NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]([C:44]#[C:43][CH:42]([O:45][CH2:46][CH3:47])[O:41][CH2:39][CH3:40])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 11773TriphenylarsineHCID 662853,3-DiethoxypropyneHCID 21226206Ethyl acetate hexaneHCID 86695590tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate

Product 1

HCID 86695595tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

To tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate 5 g (14.23 mmole) in toluene (42 mL) and triethylamine (8.33 mL) under nitrogen was added triphenyl arsine (4.39 g), 3,3-diethoxyprop-1-yne (3.24 mL) and Pddba (1.27 g). The contents were heated at 70 degrees for 24 hrs. After filtration through celite, the crude reaction was columned using hexane/ethyl acetate (0-20%) to afford the desired product. 3.9 g. Column chromatography of the resulting residue using hexane/ethyl acetate (0-30%) afforded tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]ethyl]carbamate. LCMS (ESI) 399 (M+H)

Workup

  1. temperatureThe contents were heated at 70 degrees for 24 hrs
  2. filtrationAfter filtration through celite
  3. customthe crude reaction

Sources & evidence

ORD record
ord-eec0785997bd4fc88ae173842e8bdea6
Source dataset
uspto-grants-2016_02
Patent number
US09260442B2

Reaction notes

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