Sodium Hydroxide → (2-Chloro-benzyl)-(5-chloro-pyrido[4,3-d]pyrimidin-2-yl)-amine

HRID 41482Notes

Reaction equation

HRID 41482 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:15](=O)[NH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[OH-].[Na+].O=P(Cl)(Cl)[Cl:25]>>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:15]([Cl:25])=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 584501722-(2-Chloro-benzylamino)-6H-pyrido[4,3-d]pyrimidin-5-one

Product 1

HCID 58450134(2-Chloro-benzyl)-(5-chloro-pyrido[4,3-d]pyrimidin-2-yl)-amineYield 100%

Conditions

Temperature
90 °C

Procedure

2-(2-Chloro-benzylamino)-6H-pyrido[4,3-d]pyrimidin-5-one 8 (3.00 g, 10.5 mmol) was dissolved in POCl3 (30 mL) and stirred at 90° C. for 15 h. The reaction mixture was carefully poured into ice water and the pH was adjusted to 8 adding 2 N NaOH solution. The precipitate formed was filtered off and dried in vacuo. The product was purified by crystallization from diethyl ether to yield in a colorless solid (3.18 g, 10.4 mmol, 100%).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. customdried in vacuo
  4. customThe product was purified by crystallization from diethyl ether

Sources & evidence

ORD record
ord-4636cedd03bb47f09158caff8548b507
Source dataset
uspto-grants-2013_09
Patent number
US08530650B2

Reaction notes

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