Phosphorus oxychloride → HCID 46913081, compound

HRID 535979Notes

Reaction equation

HRID 535979 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=O)[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1)=O.O=P(Cl)(Cl)[Cl:30]>CN(C=O)C>[CH2:21]([N:19]1[CH:20]=[C:16]([C:14]2[NH:13][C:3]3[C:4](=[O:12])[N:5]([CH2:9][CH2:10][CH3:11])[C:6]([Cl:30])=[N:7][C:2]=3[N:1]=2)[CH:17]=[N:18]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 671346871-Benzyl-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

Product 1

HCID 46913081HCID 46913081, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
127.5 °C

Procedure

A mixture of 1-benzyl-1H-pyrazole-4-carboxylicacid(6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.5 g, 13.5 mmol), POCl3 (10 ml) and DMF (0.1 ml) were heated at 125-130° C. for 20 hours. Reaction mixture was cooled to 20-25° C. It was then concentrated under vacuum. The residue was triturated with diethyl ether, dried. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 2 to 4% methanol in DCM as an eluent to obtain 8-(1-Benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.04 g, 8%) as a pale brown solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C
  3. concentrationIt was then concentrated under vacuum
  4. customThe residue was triturated with diethyl ether
  5. customdried
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-00f44be746984c84b2dc82177b8c0c30
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

Loading…