Ethanol → HCID 86723517, compound

HRID 2201282Notes

Reaction equation

HRID 2201282 reaction equation
[C:1]([C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.C(N(CC)CC)C.[NH2:31][CH2:32][C@H:33]([OH:35])[CH3:34]>C(Cl)Cl.O>[OH:35][C@H:33]([CH3:34])[CH2:32][N:31]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:9]2[C:14]([N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]2=[O:20])=[CH:15]1

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 439938(2R)-1-aminopropan-2-olHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 86723517HCID 86723517, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (1 g 2.97 mmol) was added to a microwave vial (10-25 mL) equipped with a stirrer bar. To the vial was added ethanol (10 ml) followed by triethylamine (0.41 ml, 2.97 mmol) and (R)-1-aminopropan-2-ol (commercial). (223 mg, 2.97 mmol) The vial was heated to 100° C. in a microwave reactor for 1 h. The ethanol was removed in vacuo to yield a solid. The solid was dissolved in DCM and water added. The DCM water mixture was separated and the aqueous extracted with DCM (×2). The organics were combined, washed with water and passed through a hydrophobic frit. The solvent was removed in vacuo to yield the title compound as a pale yellow solid.

Workup

  1. customequipped with a stirrer bar
  2. customThe ethanol was removed in vacuo
  3. customto yield a solid
  4. customThe DCM water mixture was separated
  5. extractionthe aqueous extracted with DCM (×2)
  6. washwashed with water
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-65d72c9970044e6b9618fe21de4ae59a
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…