Water → 1,4-Dihydro-5-[5-bromoacetyl)-2-ethoxyphenyl]-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 21951Notes

Reaction equation

HRID 21951 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[NH:15][C:16](=[O:27])[C:17]2[N:22]([CH3:23])[N:21]=[C:20]([CH2:24][CH2:25][CH3:26])[C:18]=2[N:19]=1)[CH3:6].[Br:28][CH2:29][C:30](Br)=[O:31].O>ClCCl>[Br:28][CH2:29][C:30]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:5][CH3:6])=[C:9]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[N:22]([CH3:23])[N:21]=[C:20]([CH2:24][CH2:25][CH3:26])[C:18]=3[N:19]=2)[CH:10]=1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 1354014775-(2-Ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-7-pyrimidinone

Product 1

HCID 1357385501,4-Dihydro-5-[5-bromoacetyl)-2-ethoxyphenyl]-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium trichloride (12.8 g, 0.096 mol) was added portionwise over 1 hour to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (10.0 g, 0.032 mol) and bromoacetyl bromide (5.6 ml, 0.064 mol) in dichloromethane (150 ml) at 0° C. After 18 hours at room temperature, the reaction mixture was poured into ice and water (400 g) and the resulting mixture stirred vigorously. The organic phase was separated and the aqueous phase further extracted with dichloromethane (2×100 ml). The organic solutions were combined, dried (Na2SO4) and evaporated under vacuum to give an off-white solid, trituration of which from ether gave the title compound as a white solid (10.87 g, 78%), m.p. 159°-160° C. Found: C,52.54; H,4.88; N,12.78. C19H21BrN4O3 requires C,52.67; H,4,88; N,12.93%.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase further extracted with dichloromethane (2×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customto give an off-white solid, trituration of which from ether

Sources & evidence

ORD record
ord-28361130068445d99356b3a5ecd38c94
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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