Triethylamine → HCID 11499906, compound

HRID 1678259Notes

Reaction equation

HRID 1678259 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>O1CCOCC1.O>[CH3:24][O:23][C:19](=[O:22])[CH2:20][S:21][C:4]1[C:5]([CH:9]=[O:10])=[C:6]([Cl:8])[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehyde

Product 1

HCID 11499906HCID 11499906, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-amino-4,6-dichloro-5-pyrimidinecarbaldehyde (Apin, 2.00 g, 10.4 mmol) in dioxane (20 mL) was added triethylamine (1.60 mL, 11.5 mmol) and methyl thioglycolate (1.90 mL, 21.2 mmol). After about 3 hours, the reaction mixture was diluted with water (30 mL) and then filtered, washed with additional water to give (2-amino-6-chloro-5-formyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester (1.801 g, 66%) as a yellow solid; RP-HPLC (Table 1, Method a) Rt 1.85 min, m/z (ESI+) 262.0 (M+H)+.

Workup

  1. filtrationfiltered
  2. washwashed with additional water

Sources & evidence

ORD record
ord-16cd81df46ce4d8798d32d9de66798c9
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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