Sodium Bicarbonate → 8-[(4-Bromophenyl)methyl]-4-methyl-2-methoxymethyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129009Notes

Reaction equation

HRID 129009 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12]CC)=O)=[C:6]([CH3:15])[N:5]=[C:4]([CH2:16][O:17][CH3:18])[N:3]=1.Cl.[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(O)CCC>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:26]2[C:2]3[N:3]=[C:4]([CH2:16][O:17][CH3:18])[N:5]=[C:6]([CH3:15])[C:7]=3[CH2:8][CH2:9][C:10]2=[O:12])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27240964-Bromobenzylamine hydrochlorideHCID 19372999Ethyl 3-(4-Chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionate

Product 1

HCID 149168398-[(4-Bromophenyl)methyl]-4-methyl-2-methoxymethyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-oneYield 73.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 3-(4-chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionate (3.6 g, 0.013 mol), 4-bromobenzylamine hydrochloride (3.0 g, 0.013 mol), NaHCO3 (2.4 g, 0.028 mol), and nBuOH (25 mL) was heated under reflux for 24 h. The mixture was concentrated, taken up in water, and extracted with CH2Cl2. The combined extracts were dried (MgSO4) and concentrated to give a brown oil. Purification by flash chromatography (5% MeOH/CH2Cl2) gave 3.6 g (72%) of product as an off-white solid, mp 64°-66° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customPurification by flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-83ecdc475cbd4350ac3d23162a740bd2
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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