Water → 4-(6-Methoxy-quinazolin-4-yloxymethyl)-cyclohexanone

HRID 1354222Notes

Reaction equation

HRID 1354222 reaction equation
C(N(CC)CC)C.N1C(=O)CC[C@H]1C(O)=O.[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2[O:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]1.O>CS(C)=O>[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2[O:29][CH2:30][CH:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 211046304-(6-Methoxy-quinazolin-4-yloxymethyl)-cyclohexanol

Product 1

HCID 211046314-(6-Methoxy-quinazolin-4-yloxymethyl)-cyclohexanone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triethylamine (10 ml, 71 mmol) and then, in portions, Pyr.SO3 (5.8 g, 36 mmol), were added at 0° C. to a solution of 4-(6-methoxy-quinazolin-4-yloxymethyl)-cyclohexanol (2.88 g, 10 mmol) in DMSO (30 ml). The reaction mixture was stirred at that temperature for 15 minutes and then allowed to come to room temperature. After 2 hours, water (300 ml) was added. The aqueous phase was extracted with ether (3×150 ml). The combined organic phases were washed with saturated sodium chloride solution, dried over MgSO4 and concentrated. The crude product was purified by chromatography on silica gel (EtOAc/hex 1/2).

Workup

  1. customto come to room temperature
  2. waitAfter 2 hours
  3. extractionThe aqueous phase was extracted with ether (3×150 ml)
  4. washThe combined organic phases were washed with saturated sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on silica gel (EtOAc/hex 1/2)

Sources & evidence

ORD record
ord-345c55533fd44f4f9ffd94a869e5a555
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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