Methanol → HCID 23446610, compound

HRID 1841614Notes

Reaction equation

HRID 1841614 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.CO.[CH3:34][N:35]([CH3:61])[CH2:36][CH2:37][CH2:38][C:39]#[C:40][C:41]1[CH:42]=[N:43][C:44]([NH:47][S:48]([C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][CH:52]=2)(=[O:50])=[O:49])=[N:45][CH:46]=1>C1COCC1>[CH3:61][N:35]([CH3:34])[CH2:36][CH2:37][CH2:38][C:39]#[C:40][C:41]1[CH:42]=[N:43][C:44]([N:47]([CH3:1])[S:48]([C:51]2[CH:52]=[CH:53][C:54]([C:57]([F:60])([F:58])[F:59])=[CH:55][CH:56]=2)(=[O:49])=[O:50])=[N:45][CH:46]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 23446677HCID 23446677, compound

Product 1

HCID 23446610HCID 23446610, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 127 mg (0.485 mmol) triphenylphosphine in 0.5 ml THF was treated at 0° C. with 0.075 ml (0.485 mmol) DEAD, then with 0.016 ml (0.388 mmol) methanol and finally with 80 mg (0.19 mmol) of N-[5-(5-Dimethylamino-pent-1-ynyl)-pyrimidin-2-yl]-4-trifluoromethyl-benzenesulfonamide in 0.3 ml THF. The reaction mixture was stirred over night at RT, evaporated and extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phases were dried over Na2SO4, evaporated and purified by flash column chromatography on silica gel with CH2Cl2/MeOH (99:1 to 95:5) to yield 19 mg (23%) of N-[5-(5-Dimethylamino-pent-1-ynyl)-pyrimidin-2-yl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 427 (MH+).

Workup

  1. customevaporated
  2. extractionextracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phases were dried over Na2SO4
  4. customevaporated
  5. custompurified by flash column chromatography on silica gel with CH2Cl2/MeOH (99:1 to 95:5)

Sources & evidence

ORD record
ord-a0278589a59c41269805754ca7246b8e
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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