Carbon Tetrachloride → HCID 86695235, compound

HRID 1504075Notes

Reaction equation

HRID 1504075 reaction equation
O[C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:41]>ClCCCl>[Cl:41][C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 178453129HCID 178453129, compound

Product 1

HCID 86695235HCID 86695235, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl N-(2-[4-hydroxythieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (2.3 g, 7.79 mmol, 1.00 equiv) in DCE (300 mL) was added PPh3 (4.1 g, 15.63 mmol, 2.00 equiv). The solution was stirred for 1 h at room temperature under nitrogen. Then CCl4 (3.6 g, 23.38 mmol, 3.00 equiv) was added and the resulting solution was stirred at 72° C. overnight. After cooling, the resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5 to 1:3) to give tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (1.0 g) as a light yellow solid. MS (ES): m/z 314 and 316 (M+H)+.

Workup

  1. stirringthe resulting solution was stirred at 72° C. overnight
  2. temperatureAfter cooling
  3. concentrationthe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-53a80f742af641398a809b37d408ba48
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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