Phosphorus oxychloride → 4-Chloro-6-(methylthio)thieno[3,2-d]pyrimidine

HRID 2408975Notes

Reaction equation

HRID 2408975 reaction equation
[CH3:1][S:2][C:3]1[S:11][C:10]2[C:9](=O)[NH:8][CH:7]=[N:6][C:5]=2[CH:4]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:9]1[C:10]2[S:11][C:3]([S:2][CH3:1])=[CH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136378636HCID 136378636, compound

Product 1

HCID 594244514-Chloro-6-(methylthio)thieno[3,2-d]pyrimidineYield 81%

Procedure

A mixture of 6-(methylthio)thieno[3,2-d]pyrimidin-4(3H)-one (900 mg) and phosphorous oxychloride (10 mL) was refluxed for 3 h. The reaction mixture was attained to rt and poured into ice cold water and stirred for 10 min. The precipitated solid was filtered, washed with water and dried to give the product as an off-white color solid (800 mg, 81%), mp 138-140° C. 1H NMR (400 MHz, CDCl3): δ 8.87 (1H, s), 7.25 (1H, s), 2.72 (3H, s).

Workup

  1. temperaturewas refluxed for 3 h
  2. customwas attained to rt
  3. additionpoured into ice cold water
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5ac84046158a4b59a4fbd0b1256a8beb
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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