Phosphorus oxychloride → HCID 86673333, compound

HRID 525073Notes

Reaction equation

HRID 525073 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:15]2[C:14](O)=[N:13][CH:12]=[N:11][C:10]=2[S:9][CH:8]=1.P(Cl)(Cl)([Cl:19])=O>O1CCOCC1>[Cl:19][C:14]1[C:15]2[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][S:9][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518068HCID 178518068, compound

Product 1

HCID 86673333HCID 86673333, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A 100-mL round-bottom flask was charged with 5-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-ol (2 g, 8.72 mmol, 1.00 equiv) and dioxane (30 mL). This was followed by the addition of phosphoroyl trichloride (4.0 g, 26.09 mmol, 2.99 equiv), in portions at room temperature. The resulting solution was stirred overnight at 110° C. The resulting mixture was concentrated under vacuum. The residue was then quenched by the addition of 50 mL of water/ice. The pH value of the solution was adjusted to 8 with saturated aqueous sodium bicarbonate. The solids were collected by filtration and dried under vacuum. This resulted in 1.0 g (46%) of 2-[4-chlorothieno[2,3-d]pyrimidin-5-yl]pyridine as a gray solid. MS: m/z 248 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customThe residue was then quenched by the addition of 50 mL of water/ice
  3. filtrationThe solids were collected by filtration
  4. customdried under vacuum
  5. customThis resulted in 1.0 g (46%) of 2-[4-chlorothieno[2,3-d]pyrimidin-5-yl]pyridine as a gray solid

Sources & evidence

ORD record
ord-ec3f3443555741cf889516edf6ec45b3
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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