Triethylamine → 1-[4-[4-[(3S)-3-Methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea

HRID 2353693Notes

Reaction equation

HRID 2353693 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:6]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:30]=[CH:29][O:28][N:27]=3)=[O:24])=[CH:18][CH:17]=2)[N:4]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:15][C@H:10]1[CH2:11][O:12][CH2:13][CH2:14][N:9]1[C:7]1[CH:8]=[C:3]([CH2:2][O:1][S:39]([CH3:38])(=[O:41])=[O:40])[N:4]=[C:5]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:30]=[CH:29][O:28][N:27]=3)=[O:24])=[CH:20][CH:21]=2)[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 593800101-[4-[4-(hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea

Product 1

HCID 593801381-[4-[4-[(3S)-3-Methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-[4-(Hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea (300 mg) was partially dissolved in DCM (10 mL) and triethylamine (0.153 mL) and the solution was cooled to 0° C. Methane sulfonyl chloride was added (0.086 mL) and the reaction was stirred for 45 mins at RT. The reaction was then washed with water (2 mL) and dried over magnesium sulphate. The solution was vacuumed to dryness to give the desired material as a yellow solid.

Workup

  1. washThe reaction was then washed with water (2 mL)
  2. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-17c77c95e06045529cabe08d23092589
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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