Benzyl Alcohol → HCID 51038392, compound

HRID 1908975Notes

Reaction equation

HRID 1908975 reaction equation
[N:1]1[CH:6]=[C:5]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH:4]=[N:3][CH:2]=1.[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:3]1[CH:4]=[C:5]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH:9]=2)[CH:6]=[N:1][CH:2]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67052541HCID 67052541, compound

Product 1

HCID 51038392HCID 51038392, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(Pyrimidin-5-yloxy)picolinic acid (1.43 g, 6.58 mmol, 1.00 eq), benzyl alcohol (1.02 mL, 9.88 mmol, 1.50 eq), PS—PPh3 (5.51 g, 14.5 mmol, 2.20 eq) and THF (66 mL) were added to a flame-dried round-bottom flask. The mixture was cooled to 0° C. and diisopropyl azodicarboxylate (2.07 mL, 10.5 mmol, 1.60 eq) was added dropwise. The reaction was allowed to warm to rt and stirred for 1 h. The reaction was filtered and washed with EtOAc. The combined organics were concentrated in vacuo and purified by flash chromatography on silica gel to afford 750 mg (37%) of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 8.87 (s, 2H), 8.64 (d, J=5.7 Hz, 1H), 7.66 (d, J=2.5 Hz, 1H), 7.47-7.40 (m, 2H), 7.40-7.38 (m, 1H), 7.38-7.32 (m, 3H), 5.36 (s, 1H); [M+1]+: 308.1.

Workup

  1. temperatureto warm to rt
  2. filtrationThe reaction was filtered
  3. washwashed with EtOAc
  4. concentrationThe combined organics were concentrated in vacuo
  5. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6788a37cf6dc4c5180e4354aeab5b19b
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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