Triethylamine → HCID 178504965, compound

HRID 2194590Notes

Reaction equation

HRID 2194590 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:13][C@H:14]3[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16][CH2:15]3)[N:7]=2)[CH2:2]1.CCN(CC)CC.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[Br:12][C:11]1[C:6]([O:5][CH:3]2[CH2:2][N:1]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:4]2)=[N:7][C:8]([NH:13][C@H:14]2[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16][CH2:15]2)=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178461297HCID 178461297, compound

Product 1

HCID 178504965HCID 178504965, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(azetidin-3-yloxy)-5-bromo-N-(cis-4-methylcyclohexyl)-pyrimidin-2-amine (1.24 g, 3.64 mmol) and Et3N (0.6 mL, 3.64 mmol) in DCM (20 mL) at 0° C. was added methanesulfonyl chloride (417 mg, 3.64 mmol). The mixture was stirred at 0° C. for 5 h, diluted by DCM, washed with saturated aqueous sodium carbonate solution and water, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, eluted by 1% methanol in DCM) to give the title compound as a white solid (1.3 g, 85% yield). MS (ESI) m/z: Calc. 418.1 (M+). Found: 420.1 (M++2).

Workup

  1. washwashed with saturated aqueous sodium carbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (silica gel, eluted by 1% methanol in DCM)

Sources & evidence

ORD record
ord-ef92da6e8dbe453aa25be66cc2350e5b
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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