Carbon Tetrachloride → tert-Butyl 4-chloro-2-(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

HRID 2406218Notes

Reaction equation

HRID 2406218 reaction equation
O[C:2]1[C:3]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:4]=2[N:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:43]>ClC(Cl)C>[Cl:43][C:2]1[C:3]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:4]=2[N:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 178451641HCID 178451641, compound

Product 1

HCID 71742291tert-Butyl 4-chloro-2-(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

tert-Butyl 4-hydroxy-2-(trifluoromethyl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (5.12 g, 16.05 mmol) was combined with triphenylphosphine (8.42 g, 32.1 mmol) and stirred in dichloroethane (160 mL) at ambient temperature for 15 minutes, and then carbon tetrachloride (7.41 g, 48.1 mmol) was added. The reaction was stirred at 70° C. for 3 hours, cooled to room temperature, and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (elution gradient from 0% to 3% methanol/DCM) to afford the title compound as a clear oil (5.22 g, 86% yield). MS (ESI) m/e (M−H)−=336.3.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by flash chromatography on silica gel (elution gradient from 0% to 3% methanol/DCM)

Sources & evidence

ORD record
ord-05e6356bac254c7a82f80c0a215903bf
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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