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Sodium hydride → 2-amino-8-(3-bromobenzyl)-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3228
Notes
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Reaction equation

HRID 3228 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[NH:10][C:8]=2[N:9]=1.[Br:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>CN(C)C=O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])[C:11](=[O:22])[N:10]([CH2:27][C:26]3[CH:29]=[CH:30][CH:31]=[C:24]([Br:23])[CH:25]=3)[C:8]=2[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

Product 1

HCID 115257882-amino-8-(3-bromobenzyl)-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 58%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

To a suspension of NaH (60% in mineral oil, 38 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (200 mg, 0.65 mmol). The mixture was heated at 50° C. for 20 minutes resulting in a clear solution. The heating mantle was removed, and 3-bromobenzyl bromide (240 μL, 0.96 mmol) was added. After 10 minutes, the reaction mixture was poured onto 30 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The solid was purified by flash chromatography, eluting with 1:1 hexane:ethyl acetate, then dried in vacuo to provide 178 mg (58%) of 2-amino-8-(3-bromobenzyl)-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one; mp softens at 195° C., melts at 215° C.

Workup

  1. customresulting in a clear solution
  2. customThe heating mantle was removed
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with water
  5. customThe solid was purified by flash chromatography
  6. washeluting with 1:1 hexane
  7. dry with materialethyl acetate, then dried in vacuo

Sources & evidence

ORD record
ord-d37a984a916b40a38246819bac9f0f12
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733914

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes