2,4-Dichlorophenol → HCID 69710235, compound

HRID 392102Notes

Reaction equation

HRID 392102 reaction equation
Cl[C:2]1[C:3]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[OH:29].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[O:29][C:2]1[C:3]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86583989HCID 86583989, compound

Product 1

HCID 69710235HCID 69710235, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-chloro-2-methylthio-5,6,7,8-tetrahydropyridino[4,3-d]pyrimidine-6-carboxylate (100 mg, 0.317 mmol), 2,4-dichlorophenol (57 mg, 0.348 mmol) and sodium bis(trimethylsilyl)amide (1.0 M solution in THF, 412 μl, 0.412 mmol) in tetrahydrofuran (2 ml) was heated at reflux over night. The mixture was partitioned between ethyl acetate and water. Organic layer was separated and washed with brine, dried (MgSO4) and filtered. Concentration of filtrate afforded crude product (180 mg), which was purified by flash chromatography (0.5% methanol in dichloromethane as eluent) to give tert-butyl 4-(2,4-dichlorophenoxy)-2-methylthio-5,6,7,8-tetrahydropyridino[4,3-d]pyrimidine-6-carboxylate as a white foam (52 mg, yield 37%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customConcentration of filtrate afforded crude product (180 mg), which
  9. customwas purified by flash chromatography (0.5% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-d0e01b086be441fc9c1c323dbbc30b3a
Source dataset
uspto-grants-2004_10
Patent number
US06800632B2

Reaction notes

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