Triphenylphosphine → Benzyl 3-[4-(5-chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate

HRID 1027714Notes

Reaction equation

HRID 1027714 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:32][C:33]1[N:34]=[CH:35][C:36]2[N:41]=[C:40]([C:42]3[CH:47]=[C:46]([CH3:48])[C:45]([OH:49])=[C:44]([CH3:50])[CH:43]=3)[O:39][C:37]=2[N:38]=1.O[CH:52]1[CH2:55][CH:54]([C:56]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[O:57])[CH2:53]1>O1CCCC1.C(N(CC)CC)C>[Cl:32][C:33]1[N:34]=[CH:35][C:36]2[N:41]=[C:40]([C:42]3[CH:43]=[C:44]([CH3:50])[C:45]([O:49][CH:52]4[CH2:55][CH:54]([C:56]([O:58][CH2:59][C:60]5[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=5)=[O:57])[CH2:53]4)=[C:46]([CH3:48])[CH:47]=3)[O:39][C:37]=2[N:38]=1

Participants

7

Reactant 4

HCID 11776Triphenylphosphine3×HCID 220568ethyl N-ethoxycarbonyliminocarbamate3×HCID 22934789Benzyl 3-hydroxycyclobutane-1-carboxylateHCID 1363977474-(5-Chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenol

Product 1

HCID 86675955Benzyl 3-[4-(5-chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

At 0° C., 1.14 g of triphenylphosphine and 0.69 ml of diethyl azodicarboxylate were initially charged in 30 ml of tetrahydrofuran, and the mixture was stirred for 15 min. 1.00 g of 4-(5-chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenol, 0.61 ml of triethylamine and 0.90 g of benzyl 3-hydroxycyclobutanecarboxylate were then added, and the reaction was stirred under argon, initially at room temperature for 6 h. Another 1.14 g of triphenylphosphine and 0.69 ml of diethyl azodicarboxylate were then added, and the reaction was stirred for 12 h. After another addition of 1.14 g of triphenylphosphine and 0.69 ml of diethyl azodicarboxylate and 2 further hours of reaction time at room temperature, the reaction was concentrated and the resulting residue was purified by flash chromatography (silica gel, heptane/ethyl acetate). This gave 1.45 g (86%) of the title compound.

Workup

  1. stirringthe reaction was stirred under argon, initially at room temperature for 6 h
  2. stirringthe reaction was stirred for 12 h
  3. concentrationthe reaction was concentrated
  4. customthe resulting residue was purified by flash chromatography (silica gel, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-d74fe40cb766496b9f32d2512e429c7c
Source dataset
uspto-grants-2014_05
Patent number
US08735402B2

Reaction notes

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