Dichloromethane → 1,3-Dimethyl-5-[(prop-2-yn-1-yl)amino]pyrimidine-2,4(1H,3H)-dione

HRID 467849Notes

Reaction equation

HRID 467849 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.ClCCl.[CH2:15](Br)[C:16]#[CH:17]>CO>[CH3:8][N:6]1[CH:7]=[C:2]([NH:1][CH2:17][C:16]#[CH:15])[C:3](=[O:11])[N:4]([CH3:10])[C:5]1=[O:9]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7842Propargyl bromideHCID 2507115-amino-1,3-dimethylpyrimidine-2,4(1h,3h)-dione

Product 1

HCID 135464431,3-Dimethyl-5-[(prop-2-yn-1-yl)amino]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Step 1 intermediate (1.4 g, 9.023 mmol) in 1:1 mixture of dichloromethane and methanol (28 mL) was added propargyl bromide (1.4 mL) and the mixture was stirred at room temperature for 2 h. Reaction mixture was filtered through celite bed and washed with methanol. The filtrate was concentrated under reduced pressure to give 500 mg of the product.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite bed
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-442d4893fa8e4aedaf2b97ef37da94fd
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

Loading…