Phosphorus oxychloride → N-(4,6-Dichloropyrido[3,2-d]pyrimidin-2-yl)acetamide

HRID 1517425Notes

Reaction equation

HRID 1517425 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8]2[N:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.O=P(Cl)(Cl)[Cl:27]>O1CCOCC1>[C:1]([NH:4][C:5]1[N:6]=[C:7]([Cl:27])[C:8]2[N:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 86630378HCID 86630378, compound

Product 1

HCID 57698319N-(4,6-Dichloropyrido[3,2-d]pyrimidin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-acetamido-6-chloro-pyrido[3,2-d]pyrimidine (1.19 g, 5 mmol), N,N-diisopropylethylamine (2.6 ml, 15 mmol) and POCl3 (0.7 ml, 7.5 mmol) in dioxane (50 ml), was stirred at room temperature for 1 hour. After concentration under reduced pressure, the residue was redissolved in dichloromethane (500 ml) and extracted with cold water (200 ml) till pH=6-7. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield the crude title compound which was characterised as follows: MS (m/z): 257, 259 ([M+H]+, 100). This compound was used for further reactions without any purification.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was redissolved in dichloromethane (500 ml)
  3. extractionextracted with cold water (200 ml) till pH=6-7
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12f134321068491e9fcf614e511a30f6
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

Loading…