Carbon Tetrachloride → HCID 20554358, compound

HRID 1106034Notes

Reaction equation

HRID 1106034 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][CH:20]([CH3:22])[CH3:21])=[N:8][CH:9]=[N:10][CH:11]=1)=O)C.[OH-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>O1CCOCC1>[CH:20]([N:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:7]2[N:8]=[CH:9][N:10]=[CH:11][C:6]=2[C:4]1=[O:3])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 20554379HCID 20554379, compound

Product 1

HCID 20554358HCID 20554358, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

12.7 g (0.03 mol) of 5-ethoxycarbonyl-4-(2-isopropylaminoanilino)pyrimidine in 42.2 ml of a 0.1 N. aqueous sodium hydroxide solution are heated for 1 hour under reflux. The solvent is removed on a rotary evaporator and the crystalline residue is dried in vacuo at 60° C. 28.9 g (0.11 mol) of triphenylphosphine and 16.9 g (0.11 mol) of carbon tetrachloride are added to the dry product, dissolved in 150 ml of absolute dioxan, and the mixture is stirred for 5 hours at 80° C. The solvent is removed on a rotary evaporator, and the oily residue which remains is chromatographed on neutral silica gel using 99:1 methylene chloride/methanol as the eluant; yield: 6.3 g, with m.p. 204° to 206° C. (from isopropanol).

Workup

  1. temperatureunder reflux
  2. customThe solvent is removed on a rotary evaporator
  3. customthe crystalline residue is dried in vacuo at 60° C
  4. customThe solvent is removed on a rotary evaporator
  5. customthe oily residue which remains is chromatographed on neutral silica gel using 99:1 methylene chloride/methanol as the eluant

Sources & evidence

ORD record
ord-876eb083e2f64d55bf0c3173954f0ea4
Source dataset
uspto-grants-1982_01
Patent number
US04311700

Reaction notes

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