Benzocaine → Ethyl 4-(((2-acetamido-4-oxo-3,4-dihydropteridin-6-yl)methyl)amino)benzoate

HRID 1729881Notes

Reaction equation

HRID 1729881 reaction equation
CN(C)C=O.[C:6]([NH:9][C:10]1[N:19]=[C:18]([OH:20])[C:17]2[C:12](=[N:13][CH:14]=[C:15]([CH:21]=O)[N:16]=2)[N:11]=1)(=[O:8])[CH3:7].[NH2:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1.B.CNC>C(O)(=O)C>[C:6]([NH:9][C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[N:13][CH:14]=[C:15]([N:16]=2)[CH2:21][NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:33][CH:34]=2)[N:11]=1)(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 6228DimethylformamideHCID 6330borane;N-methylmethanamineHCID 178474471HCID 178474471, compound

Product 1

HCID 136354639Ethyl 4-(((2-acetamido-4-oxo-3,4-dihydropteridin-6-yl)methyl)amino)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 3.07 g (10 mmole) of the dimethylformamide solvate of 2-acetamido-4-hydroxypteridine-6-aldehyde, 3.30 g (20 mmole) of ethyl p-aminobenzoate and 50 ml of glacial acetic acid is stirred at ambient temperature for 30 minutes. To the resulting suspension is added dropwise 1.00 g of dimethylamine borane in 15 ml of acetic acid. The mixture is stirred for an additional 20 minutes, heated to 60° C for 10 minutes and cooled to 25° C. The precipitate is collected by filtration, washed with acetic acid and ether and then dried. The crude product is crystallized from 50 ml of dimethylformamide, with dilution by 20 ml ether, to yield ethyl N2 -acetylpteroate.

Workup

  1. stirringThe mixture is stirred for an additional 20 minutes
  2. temperatureheated to 60° C for 10 minutes
  3. temperaturecooled to 25° C
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with acetic acid and ether
  6. customdried
  7. customThe crude product is crystallized from 50 ml of dimethylformamide, with dilution by 20 ml ether

Sources & evidence

ORD record
ord-66528ccb9bff4b5aa1ce8b9a790b1d1b
Source dataset
uspto-grants-1976_11
Patent number
US03989812

Reaction notes

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