Methanol → 7-Bromo-2-chloro-4-(4-morpholinyl)-thieno[3,2-d]pyrimidine

HRID 334152Notes

Reaction equation

HRID 334152 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.CO.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8083MorpholineHCID 183264227-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 534387087-Bromo-2-chloro-4-(4-morpholinyl)-thieno[3,2-d]pyrimidineYield 35.9%

Procedure

7-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine (2.9 g, 10.0 mmol) was dissolved in methanol (100 mL, 2000 mmol) and added morpholine (2 mL, 22 mmol) and let the reaction mixture stir for 1.5 h. Complete reaction confirmed by LCMS. Concentrated in vacuo and diluted with water. Extracted with DCM and concentrated in vacuo again. The product was purified by silica gel chromatography (0 to 100% ethyl acetate/heptanes) on the CombiFlash® Rf system and concentrated in vacuo to give 4-(7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine (1.2 g, 35% yield). 1H NMR (400 MHz, CDCl3) δ 7.78 (s, 1H), 4.01 (m, 4H), 3.85 (m, 4H)

Workup

  1. customComplete reaction
  2. concentrationConcentrated in vacuo
  3. additiondiluted with water
  4. extractionExtracted with DCM
  5. concentrationconcentrated in vacuo again
  6. customThe product was purified by silica gel chromatography (0 to 100% ethyl acetate/heptanes) on the CombiFlash® Rf system
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4dba2cbbfb94825a30785f3dd6d5bdf
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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