Bromine → 6-Bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine

HRID 19572

Reaction equation

HRID 19572 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[N:10]=[CH:11][C:12]3[CH:17]=[CH:16][S:15][C:13]=3[N:14]=2)[CH2:3][CH2:2]1.[Br:18]Br>C(Cl)Cl>[Br:18][C:16]1[S:15][C:13]2[N:14]=[C:9]([CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:10]=[CH:11][C:12]=2[CH:17]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 685591422-(2-Morpholinoethyl)thieno[2,3-d]pyrimidine

Product 1

HCID 685604506-Bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine (1.0 g, 3.79 mmol) in DCM (50 mL) at 0° C. was added a solution of bromine (1.2 eq) in DCM (3 mL) dropwise. The resulting solution was stirred at 0° C. for 30 min. The reaction mixture was quenched with saturated solution of NH4Cl. The layers were separated, and the aqueous layer was extracted with DCM (3×25 mL). Organic layers were combined, washed with brine (2×30 mL), dried over MgSO4, filtered and concentrated to provide the title compound (0.910 g). MS (ES+): 345 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with saturated solution of NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (3×25 mL)
  4. washwashed with brine (2×30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d7434df835e140b7b6114cbf48afc7ca
Source dataset
uspto-grants-2010_06
Patent number
US07745449B2

Linked notes

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