Pyridine → [2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl acetate

HRID 1508715Notes

Reaction equation

HRID 1508715 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([CH2:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:10]=2)=[CH:4][C:3]=1[CH2:24][OH:25].[C:26](Cl)(=[O:28])[CH3:27].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[C:26]([O:25][CH2:24][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[C:14]([CH2:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:10]=2)[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 90112603[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol

Product 1

HCID 90113035[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl acetateYield 72.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A 18-mL vial was charged with [2-bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol (93 mg, 0.21 mmol), acetyl chloride (100 mg, 1.27 mmol, 6 eq.). Pyridine (1 ml) was added followed by 4-(dimethylamino)pyridine (5 mg, 0.2 eq.). The resulting mixture was stirred at rt for 2 hr. Then water was (5 ml) added. The precipitate was collected and washed with water. The crude product was purified by chromatography on silica gel using dichloromethane as eluent to give the tile compound (73 mg, 72% yield).

Workup

  1. additionadded
  2. customThe precipitate was collected
  3. washwashed with water
  4. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4ef87933092a457e89f43f5a0fb30ce4
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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