Benzyl Alcohol → HCID 178522378, compound

HRID 1525224Notes

Reaction equation

HRID 1525224 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, 1-1-h, (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. The mixture was then concentrated under vacuum and the residue was purified on silica gel chromatography with the eluent of petroleum ether/ethyl acetate=1/5 (Rf=0.3) to afford the crude product, 7-a, (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).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was then concentrated under vacuum
  4. customthe residue was purified on silica gel chromatography with the eluent of petroleum ether/ethyl acetate=1/5 (Rf=0.3)

Sources & evidence

ORD record
ord-b734d1e44e4d44209feacf932e45f486
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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