N-bromobutanimide → 6-bromo-3-(3-(tert-butyldimethylsilyloxy)propyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63895Notes

Reaction equation

HRID 63895 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH3:22])=[CH:20][S:21][C:15]=2[N:14]([CH3:23])[C:13]1=[O:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([Br:32])C(=O)C1>C(Cl)Cl>[Br:32][C:20]1[S:21][C:15]2[N:14]([CH3:23])[C:13](=[O:24])[N:12]([CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[C:17](=[O:18])[C:16]=2[C:19]=1[CH3:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 131737211HCID 131737211, compound

Product 1

HCID 1317372106-bromo-3-(3-(tert-butyldimethylsilyloxy)propyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3-(tert-butyldimethylsilyloxy)propyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (3.0 g, 8.14 mmol) in DCM (30 mL) at 0° C. was added NBS (1.6 g, 8.95 mmol). The reaction was stirred at 0° C. for 2 h then diluted with DCM (100 mL) and washed with water (2×50 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography PE/EA (1:1) to give 6-bromo-3-(3-(tert-butyldimethylsilyloxy) propyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (3.4 g, 93.4% yield) as a white solid. LCMS: MH+ 448 and TR=2.917 min.

Workup

  1. washwashed with water (2×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated to a residue which
  4. customwas purified by chromatography PE/EA (1:1)

Sources & evidence

ORD record
ord-054afdd1e7bd4dffb3d686dd86de7f5d
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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