4-Toluenesulfonyl chloride → 2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

HRID 1014932Notes

Reaction equation

HRID 1014932 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([OH:17])[C:5]2[CH2:12][CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][C:4]2[C:5]3[CH2:12][CH2:11][CH2:10][C:9]4[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=4[C:6]=3[N:7]=[C:2]([NH2:1])[N:3]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178508870HCID 178508870, compound

Product 1

HCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonateYield 63.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The product from Example 4B (2.8 g, 12.3 mmol) was suspended in CH2Cl2 (100 mL), treated with TsCl (4.7 g, 24.6 mmol), 4-dimethylaminopyridine (46 mg, 1.2 mmol), and triethylamine (4.3 mL. 31 mmol). The mixture was stirred at room temperature for 16 hours, diluted with CH2Cl2, washed with H2O, dried (MgSO4), concentrated and chromatographed on silica gel eluting with EtOAc:Hexanes:CH2Cl2 (15:45:45) to provide the title product (3 g) as a white solid.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed on silica gel eluting with EtOAc:Hexanes:CH2Cl2 (15:45:45)

Sources & evidence

ORD record
ord-769c3203136e45d28ce32592b42aed08
Source dataset
uspto-grants-2011_07
Patent number
US07985745B2

Reaction notes

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