Water → HCID 118863149, compound

HRID 63883Notes

Reaction equation

HRID 63883 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]2[C:12]([CH3:15])=[CH:13][S:14][C:8]=2[N:7]([CH3:16])[C:6]1=[O:17].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH2:35]1[CH2:40][O:39][CH:38]=[CH:37][CH2:36]1.O>C(Cl)Cl>[CH3:16][N:7]1[C:8]2[S:14][CH:13]=[C:12]([CH3:15])[C:9]=2[C:10](=[O:11])[N:5]([CH2:4][CH2:3][CH2:2][O:1][CH:38]2[CH2:37][CH2:36][CH2:35][CH2:40][O:39]2)[C:6]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 118863143HCID 118863143, compound

Product 1

HCID 118863149HCID 118863149, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (9 g, 35.4 mmol) and PPTS (900 mg, 3.54 mmol) in DCM (90 mL) at 0° C. was added DHP (8.96 g, 0.106 mol) 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 and eluted with PE/EA (4:1) to give 1,5-dimethyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (11.2 g, 93.4% yield) as a yellow oil. LCMS: [MH+-THP] 255 and TR=1.473 min.

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-eba9da888119478e80378df6ecd6edac
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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