Triphenylphosphine → (2-Propyl-thiazol-5-yl)methyl 4-(5-undecyl-pyrimidin-2-yl)phenyl ether

HRID 1826554Notes

Reaction equation

HRID 1826554 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32]([C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)=[N:47][CH:48]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[CH2:56]([C:59]1[S:60][C:61]([CH2:64]O)=[CH:62][N:63]=1)[CH2:57][CH3:58]>C1COCC1>[CH2:32]([C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:50]=[CH:51][C:52]([O:55][CH2:64][C:61]3[S:60][C:59]([CH2:56][CH2:57][CH3:58])=[N:63][CH:62]=3)=[CH:53][CH:54]=2)=[N:47][CH:48]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22134228(2-Propyl-1,3-thiazol-5-yl)methanolHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 22134209(2-Propyl-thiazol-5-yl)methyl 4-(5-undecyl-pyrimidin-2-yl)phenyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A fully reacted mixture of equimolar amounts of diethyl azodicarboxylate and triphenylphosphine in THF is admixed with equimolar amounts of 4-(5-undecyl-pyrimidin-2-yl)phenol and 2-propylthiazol-5-yl-methanol (prepared by LiAlH4 reduction of methyl 2-propylthiazole-5-carboxylate). The mixture is stirred for 24 h at room temperature and then evaporated to dryness under reduced pressure. Purification by chromatography (silica gel, dichloromethane) and recrystallization affords the target compound.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customPurification
  3. customby chromatography (silica gel, dichloromethane) and recrystallization
  4. customaffords the target compound

Sources & evidence

ORD record
ord-1c2d38b5afb54b469b294cf122cf89c2
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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