Water → HCID 66588933, compound

HRID 1093233Notes

Reaction equation

HRID 1093233 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[N:10][C:11]([N:12]3[CH2:18][CH:17]4[O:19][CH:14]([CH2:15][CH2:16]4)[CH2:13]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[Br:29]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:29][C:5]1[C:6]2[C:7](=[N:8][C:9]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[N:10][C:11]=2[N:12]2[CH2:13][CH:14]3[O:19][CH:17]([CH2:16][CH2:15]3)[CH2:18]2)[N:3]([CH2:1][CH3:2])[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 66589085HCID 66589085, compound

Product 1

HCID 66588933HCID 66588933, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-ethyl-6-(4-nitrophenyl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (7.9 g)(20.8 mmol) in DMF (140 mL) was added N-bromosuccinimide (18.5 g) and heated to 85 C for 24 hr. The reaction was cooled and poured into water (1.0 L) to precipitate tan solids. The solids were filtered off and washed with water. The crude solid was purified by silica gel chromatography (EtOAc/Hexanes) to give 2.8 g of a yellow solid. MS m/z=459.2 (M+H)

Workup

  1. temperatureheated to 85 C for 24 hr
  2. temperatureThe reaction was cooled
  3. customto precipitate tan solids
  4. filtrationThe solids were filtered off
  5. washwashed with water
  6. customThe crude solid was purified by silica gel chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-16c18142a7434a8d8c5beb64dd0102a0
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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