Phosphorus oxychloride → HCID 4389052, compound

HRID 1056831Notes

Reaction equation

HRID 1056831 reaction equation
O[C:2]1[C:3]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:4]=2[N:5]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:2]1[C:3]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:4]=2[N:5]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470785HCID 178470785, compound

Product 1

HCID 4389052HCID 4389052, compound

Conditions

Temperature
0 °C

Procedure

The ethyl 2-(4-hydroxy-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate (9 g, 0.03078 mol) and phosphorous oxy-chloride (45 ml) was refluxed for 4 h. After completion of the reaction, it was concentrated under reduced pressure. The resulting residue was cooled to 0° C. To this, ice water (200 ml) was added and stirred for 30 min. Then it was basified with 25% aq. NH4OH solution slowly to pH=8. It was extracted with DCM (250 ml×3). Organic extracts were washed with water followed by brine. The separated organic layer was dried over anhydrous Na2SO4 and concentrated to get crude product. It was purified by column chromatography by using 100-200 mesh silica gel and DCM as eluent to give ethyl 2-(4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate as yellow liquid. Yield—(7 g, 73.16%); 1H-NMR: (400 MHz, CDCl3); δ=4.22-4.16 (q, 2H), 4.02 (s, 2H), 3.06 (m, 2H), 2.85-2.84 (m, 2H), 1.93-1.83 (m, 4H), 1.26-1.23 (t, 3H); LC-MS [M+H]=310.9.

Workup

  1. customAfter completion of the reaction, it
  2. concentrationwas concentrated under reduced pressure
  3. additionTo this, ice water (200 ml) was added
  4. extractionIt was extracted with DCM (250 ml×3)
  5. washOrganic extracts were washed with water
  6. dry with materialThe separated organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto get crude product
  9. customIt was purified by column chromatography

Sources & evidence

ORD record
ord-e97b2ce365fd47a4bcfd27ae5ef791cd
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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