Dimethylformamide → 4-Chlorothieno[3,2-d]pyrimidine

HRID 500755Notes

Reaction equation

HRID 500755 reaction equation
[C:1]([Cl:6])([C:3](Cl)=O)=O.CN(C=O)C.[N:12]1[C:17]2[CH:18]=[CH:19][S:20]C=2C(=O)[NH:14][CH:13]=1>O>[Cl:6][C:1]1[C:3]2[S:20][CH:19]=[CH:18][C:17]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27358214-Chlorothieno[3,2-d]pyrimidineYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (COCl)2 (7.33 mL, 84.11 mmol) in anhydrous (CH2Cl)2 (20 mL) at 0° C. under nitrogen was added DMF (4.47 mL, 57.18 mmol). After 20 min a solution of thieno[3,2-d]pyrimidin-4(3H)-one (19) (4 g, 26.28 mmol) in anhydrous (CH2Cl)2 (5 mL added drop wise to the reaction mixture which was stirred for 20 min at 0° C., warmed to room temperature over another 20 min, heated at 80° C. for 1.5 hours, and cooled to room temperature. Finally, the reaction mixture was poured into water and extracted with DCM. The extract was washed sequentially with water, brine, dried over Na2SO4, filtered and evaporated to afford the title compound 20 (4.36 g, 97% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.02 (s, 1H), 8.59 (d, J=5.2 Hz, 1H), 7.75 (d, J=5.2 Hz, 1H).

Workup

  1. temperaturewarmed to room temperature over another 20 min
  2. temperatureheated at 80° C. for 1.5 hours
  3. temperaturecooled to room temperature
  4. extractionextracted with DCM
  5. washThe extract was washed sequentially with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-83dbdf03393d41c591f6ba82300ebbdd
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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