4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine → 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimi-dinyl]-2-pyridine sulfonamide

HRID 2085079Notes

Reaction equation

HRID 2085079 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:3]=1.[K+].[CH:25]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([NH-:37])(=[O:36])=[O:35])=[N:32][CH:33]=1)([CH3:27])[CH3:26]>CS(C)=O>[CH:25]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([NH:37][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:3]=2)(=[O:36])=[O:35])=[N:32][CH:33]=1)([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 105457064,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidineHCID 1317209445-Isopropyl pyridine-2-sulfonamide potassium salt

Product 1

HCID 227293985-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimi-dinyl]-2-pyridine sulfonamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3.5 g of 4,6-dichloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine and 4.98 g of 5-isopropyl-2-pyridine sulfonamide potassium salt (Example 1, section e) in 40 ml of DMSO was stirred at room temperature for 4 h. The mixture was poured onto water and extracted twice with diethyl ether. The aqueous layer was acidified with acetic acid. The precipitate that formed was collected, washed with water and diethyl ether and dried to furnish 5.1 g of 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimi-dinyl]-2-pyridine sulfonamide as a white solid. LC-MS: tR=4.87 min, [M+1]+=513.32, [M−1]−=511.26.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted twice with diethyl ether
  3. customThe precipitate that formed
  4. customwas collected
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-1863a6d2612c4871b27753b6131fb6ed
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

Loading…