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p-Toluenesulfonic acid → 2-(4-(bis(2-hydroxyethyl)amino)phenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-one

HRID 336758
Notes
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Reaction equation

HRID 336758 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[OH:15][CH2:16][CH2:17][N:18]([CH2:27][CH2:28][OH:29])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[OH:15][CH2:16][CH2:17][N:18]([CH2:27][CH2:28][OH:29])[C:19]1[CH:26]=[CH:25][C:22]([C:23]2[NH:6][C:4](=[O:5])[C:3]3[C:7]([O:13][CH3:14])=[CH:8][C:9]([O:11][CH3:12])=[N:10][C:2]=3[N:1]=2)=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 128249654-(N,N-Bis(2-hydroxyethyl)amino)benzaldehydeHCID 23665763Sodium BisulfiteHCID 666066902-Amino-4,6-dimethoxy-nicotinamide

Product 1

HCID 1360379812-(4-(bis(2-hydroxyethyl)amino)phenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-oneYield 10.2%

Reagents, catalysts & solvents

1
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-amino-4,6-dimethoxy-nicotinamide (300 mg, 1.52 mmol) and 4-(bis-(2-hydroxyethyl)amino)-benzaldehyde (318 mg, 1.52 mmol) in N,N-dimethylacetamide (10 mL) were added NaHSO3 (297 mg, 1.67 mmol) and p-TSA (376 mg, 1.98 mmol) and the reaction mixture was heated at 150° C. for 4 h, cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with water and the solid was filtered off to give the crude product. The crude product was purified by column chromatography to give 2-(4-(bis(2-hydroxyethyl)amino)phenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-one (60 mg, 10%). Selected data: MS (ES) m/z: 387.05; MP 277-279° C.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. filtrationthe solid was filtered off
  5. customto give the crude product
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-795d2e26881b462f965756596fe42b43
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889698B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes