Dichloromethane → HCID 54383660, compound

HRID 342559Notes

Reaction equation

HRID 342559 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][C:17]2([CH2:20][OH:21])[CH2:19][CH2:18]2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)Cl.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>O>[CH3:33][S:34]([O:21][CH2:20][C:17]1([CH2:16][N:10]2[C:11](=[O:15])[C:12]([CH3:14])=[CH:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]2=[O:22])[CH2:18][CH2:19]1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54327213HCID 54327213, compound

Product 1

HCID 54383660HCID 54383660, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(1-benzyl-5-methyl-2,4-dioxo-(1H,3H)-pyrimidin-3-ylmethyl)cycloprop-1-ylmethanol (1.95 g, 6.5 mmol), triethylamine (1.32 mL, 9.5 mmol) and methylene chloride (20 mL) was cooled to between 0° and 5° C. under argon and methanesulfonyl chloride (0.69 mL, 8.85 mmol) was added slowly. The mixture was stirred cooled 2 hours at 0° to 5° C., then diluted with water (20 mL) and extracted with methylene chloride. The extract was washed with 5% sodium bicarbonate, dried (MgSO4) and concentrated to give 1-(1-benzyl-5-methyl-2,4-dioxo-(1H,3H)-pyrimidin-3-ylmethyl)cycloprop-1-ylmethyl methanesulfonate.

Workup

  1. temperaturewas cooled to between 0° and 5° C. under argon
  2. temperaturecooled 2 hours at 0° to 5° C.
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with 5% sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bcff56db6c6942ee88790fab0b77e7e4
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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