Water → 6-bromo-5-(bromomethyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl) thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63884Notes

Reaction equation

HRID 63884 reaction equation
[Br:1][C:2]1[S:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[N:8]([CH2:11][CH2:12][CH2:13][OH:14])[C:9](=[O:10])[C:4]=2[C:3]=1[CH2:18][Br:19].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH2:37]1[CH2:42][O:41][CH:40]=[CH:39][CH2:38]1.O>C(Cl)Cl>[Br:1][C:2]1[S:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:40]3[CH2:39][CH2:38][CH2:37][CH2:42][O:41]3)[C:9](=[O:10])[C:4]=2[C:3]=1[CH2:18][Br:19]

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 1188630946-bromo-5-(bromomethyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1188631026-bromo-5-(bromomethyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl) thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-5-(bromomethyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.5 g, 6.1 mmol) and PPTS (153 mg, 0.61 mmol) in DCM (25 mL) at 0° C. was added DHP (2.00 g, 24.5 mmol) dropwise. The reaction was stirred at RT for 18 h, poured into water (30 mL) and extracted with DCM (2×20 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (4:1) to give 6-bromo-5-(bromomethyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1.7 g, 56.7% yield) as a yellow oil.

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by chromatography
  6. washeluted with PE/EA (4:1)

Sources & evidence

ORD record
ord-6ea8123dde75427b8f3b780ac2c0f251
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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