Phosphorus oxychloride → HCID 86675326, compound

HRID 625043Notes

Reaction equation

HRID 625043 reaction equation
[CH2:1]([CH:3]1[C:11]2[C:10](O)=[N:9][CH:8]=[N:7][C:6]=2[CH2:5][S:4]1)[CH3:2].C(C1SC2C(O)=NC=NC=2C1)C.O=P(Cl)(Cl)[Cl:27]>ClCCCl.C(N(C(C)C)CC)(C)C>[Cl:27][C:10]1[C:11]2[CH:3]([CH2:1][CH3:2])[S:4][CH2:5][C:6]=2[N:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 178435432HCID 178435432, compoundHCID 178438241HCID 178438241, compound

Product 1

HCID 86675326HCID 86675326, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of a mixture of 5-ethyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-ol and 6-ethyl-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (2.32 g, 12.8 mmol) in 1,2-dichloroethane (50 mL) and diisopropylethylamine (4 mL) was added POCl3 (4 mL), and the mixture was refluxed overnight. The solvent was removed and the residue was purified by silica gel chromatography, eluting with Hexane/ethyl acetate (9:1-4:1) to give 4-chloro-5-ethyl-5,7-dihydrothieno[3,4-d]pyrimidine (0.49 g, 28%). 1H NMR (CDCl3, 400 MHz) δ 8.73 (s, 1H), 4.44 (m, 1H), 4.32-4.00 (m, 2H), 2.08 (m, 1H), 1.75 (m, 1H), 0.93 (m, 3H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with Hexane/ethyl acetate (9:1-4:1)

Sources & evidence

ORD record
ord-088a88eefd324e5483cd8172a3274526
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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