Phosphorus oxychloride → 4-Chloro-5,7-dihydrothieno[3,4-d]pyrimidine

HRID 625048Notes

Reaction equation

HRID 625048 reaction equation
[N:1]1[C:6]2[CH2:7][S:8][CH2:9][C:5]=2[C:4](O)=[N:3][CH:2]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:22]>ClCCCl>[Cl:22][C:4]1[C:5]2[CH2:9][S:8][CH2:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178517924HCID 178517924, compound

Product 1

HCID 457897284-Chloro-5,7-dihydrothieno[3,4-d]pyrimidineYield 81.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the 5,7-dihydrothieno[3,4-d]pyrimidin-4-ol (0.50 g, 3.2 mmol) in DCE (50 mL) was added DIEA (0.42 g, 3.2 mmol) and POCl3 (1.5 g, 9.8 mmol). The mix was refluxed overnight. After cooling, the solvent was removed and the residue was subject to silica gel chromatography, eluting with hexane/ethyl acetate (4:1) to give 4-chloro-5,7-dihydrothieno[3,4-d]pyrimidine (0.45 g, 80%). 1H NMR (CDCl3, 400 MHz) δ 8.84 (s, 1H), 4.37 (s, 2H), 4.27 (s, 2H).

Workup

  1. temperatureThe mix was refluxed overnight
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-74c8c661827b4ba39b4bdc5b2bb6a9ff
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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