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

HRID 63896Notes

Reaction equation

HRID 63896 reaction equation
[Br:1][C:2]1[S:24][C:5]2[N:6]([CH3:23])[C:7](=[O:22])[N:8]([CH2:11][CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)[C:9](=[O:10])[C:4]=2[C:3]=1[CH3:25]>Cl.CO.C(Cl)Cl>[Br:1][C:2]1[S:24][C:5]2[N:6]([CH3:23])[C:7](=[O:22])[N:8]([CH2:11][CH2:12][CH2:13][OH:14])[C:9](=[O:10])[C:4]=2[C:3]=1[CH3:25]

Participants

5

Reactant 1

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

Product 1

HCID 1188631236-bromo-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 116.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

6-bromo-3-(3-(tert-butyldimethylsilyloxy)propyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4 (1H,3H)-dione (2.4 g, 4.39 mmol) was dissolved in aq. 6N HCl (15 mL) and MeOH (15 mL). The reaction was stirred at RT for 30 min then diluted with DCM (20 mL) and washed with water (2×20 mL). The organic layer was dried over Na2SO4 and concentrated to give 6-bromo-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1.7 g, 95.5% yield) as a white solid. LCMS: MH+ 334 and TR=1.049 min. Used without further purification.

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-04f1b8fc4ccb41eca716a0ff302ab220
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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