Benzyl Alcohol → HCID 178522378, compound

HRID 1470314Notes

Reaction equation

HRID 1470314 reaction equation
[OH:1][C:2]1[C:7](C(O)=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])=CC=1.CC[N:36]([CH2:39]C)CC.[CH2:41]([OH:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:7]([NH:36][C:39](=[O:24])[O:48][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178524750HCID 178524750, compound

Product 1

HCID 178522378HCID 178522378, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid (10-c) (10 g, 46 mmol) in toluene (150 ml) was added DPPA (13.94 g, 50.6 mmol), Et3N (9.31, 92.1 mmol) and benzyl alcohol (14.93 g, 0.14 mol). The resulting mixture was heated at reflux overnight. Then the mixture was concentrated under vacuum and the residue was purified on silica gel chromatography with the eluent of petroleum ether/ethyl acetate=1/5, v/v, (Rf=0.3) to afford the crude compound 10-d (3.2 g). The sample delivered was re-purified on prep-HPLC. 1H NMR (DMSO-d6, 300 MHz): δ 8.73 (m, 1H), 8.40 (m, 2H), 8.00 (m, 1H), 7.37 (m, 6H), 5.19 (s, 1H). (M+H)+=323.1.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThen the mixture was concentrated under vacuum
  4. customthe residue was purified on silica gel chromatography with the eluent of petroleum ether/ethyl acetate=1/5
  5. customv/v, (Rf=0.3) to afford the crude compound 10-d (3.2 g)
  6. customThe sample delivered was re-purified on prep-HPLC

Sources & evidence

ORD record
ord-3f634abe062b451f9a5443a6e9243e50
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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