Phosphorus oxychloride → Methyl 2-(2-([1,1'-biphenyl]-3-yl)-7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 574347Notes

Reaction equation

HRID 574347 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:22]=[C:10]3[N:11]=[C:12]([CH3:21])[C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:14](O)[N:9]3[N:8]=2)[CH:2]=1.P(Cl)(Cl)([Cl:31])=O.C([O-])(O)=O.[Na+]>>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:22]=[C:10]3[N:11]=[C:12]([CH3:21])[C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:14]([Cl:31])[N:9]3[N:8]=2)[CH:2]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178499497HCID 178499497, compound

Product 1

HCID 86695073Methyl 2-(2-([1,1'-biphenyl]-3-yl)-7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetateYield 87.1%

Procedure

A suspension of methyl 2-(2-([1,1′-biphenyl]-3-yl)-7-hydroxy-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (748 mg, 1.998 mmol) in phosphoryl trichloride (15 ml, 1.998 mmol) was heated to reflux for 16 hrs. Concentrated to remove most of phosphoryl chloride to leave an oil, which was carefully neutralized w/sat'd NaHCO3 to PH=˜7. The precipitates was filtered and washed w/water, dried in vacuo to afford methyl 2-(2-([1,1′-biphenyl]-3-yl)-7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (720 mg, 1.741 mmol, 87% yield). The crude was used for the next reaction directly. 1H-NMR (500 MHz, CDCl3) δ ppm 2.75 (3H, s), 3.81 (3H, s), 3.96 (2H, s), 7.43-7.44 (1H, m), 7.49-7.52 (2H, m), 7.62-7.63 (1H, m), 7.74-7.78 (3H, m), 8.36-8.38 (1H, m), 8.65 (1 H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hrs
  3. concentrationConcentrated
  4. customto remove most of phosphoryl chloride
  5. customto leave an oil, which
  6. filtrationThe precipitates was filtered
  7. washwashed w/water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d2d0b0adfdf84a1c8053b780270f99bf
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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