Triphenylphosphine → HCID 22134211, compound

HRID 1826548Notes

Reaction equation

HRID 1826548 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].[F:56][C:57]1[CH:58]=[C:59]([CH2:65]O)[S:60][C:61]=1[CH2:62][CH2:63][CH3:64]>C1COCC1>[CH2:32]([C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:50]=[CH:51][C:52]([O:55][CH2:65][C:59]3[S:60][C:61]([CH2:62][CH2:63][CH3:64])=[C:57]([F:56])[CH:58]=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 221342294-Fluoro-5-propyl-thiophen-2-yl-methanolHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 22134211HCID 22134211, compound

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 4-fluoro-5-propyl-thiophen-2-yl-methanol (prepared by LiAlH4 reduction of methyl 4-fluoro-5-propyl-thiophene-2-carboxylate). After 24 h at room temperature the mixture is evaporated to dryness under reduced pressure. Purification by chromatography (silica gel, dichloromethane) and recrystallization affords the target compound.

Workup

  1. customAfter 24 h at room temperature the mixture is evaporated 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-9f4baf0151db4b03a362b88963605a4f
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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