Phosphorus oxychloride → 6-tert-Butyl-4-chlorothieno[3,2-d]pyrimidine

HRID 351407Notes

Reaction equation

HRID 351407 reaction equation
[C:1]([C:5]1[S:13][C:12]2[C:11](O)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:17])=O>C(Cl)Cl>[C:1]([C:5]1[S:13][C:12]2[C:11]([Cl:17])=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178440588HCID 178440588, compound

Product 1

HCID 27572666-tert-Butyl-4-chlorothieno[3,2-d]pyrimidineYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-tert-Butyl-thieno[3,2-d]pyrimidin-4-ol (500 mg, 2.40 mmol, 1 eq.) and phosphorous oxychloride (4.48 mL, 48.0 mmol, 20 eq.) were refluxed under nitrogen for 1.5 hours. Stripped 3× from methylene chloride then dissolved in methylene chloride and rinsed 3× with saturated NaHCO3, 1× with brine. Dried and stripped in vacuo to give 250 mg of amber solids as product. LCMS detects (M+H)+=227.

Workup

  1. washrinsed 3× with saturated NaHCO3, 1× with brine
  2. customDried

Sources & evidence

ORD record
ord-1e008c9958844bf393349840fa9d09ed
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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