2-Methoxyethanol → 6-Chloro-4-(2-methoxyethoxy)pyrido[3,2-d]pyrimidin-2-amine

HRID 1099111Notes

Reaction equation

HRID 1099111 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]=[C:13]([NH2:23])[N:14]=[C:15](N3C=NC=N3)[C:16]=2[N:17]=1.[CH3:24][O:25][CH2:26][CH2:27][OH:28]>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]=[C:13]([NH2:23])[N:14]=[C:15]([O:28][CH2:27][CH2:26][O:25][CH3:24])[C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 23665647Potassium tert-butoxideHCID 576983146-Chloro-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine

Product 1

HCID 576983626-Chloro-4-(2-methoxyethoxy)pyrido[3,2-d]pyrimidin-2-amineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Potassium tert-butoxide (4 mL; 1M in THF) was added to a suspension of 6-Chloro-4-[1,2,4]triazol-1-yl-pyrido[3,2-d]pyrimidin-2-ylamine (1 g) and 2-methoxyethanol (0.32 mL) in DCM (50 mL). After stirring at room temperature for 10 minutes, the mixture was diluted with DCM (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford 6-chloro-4-(2-methoxy-ethoxy)-pyrido[3,2-d]pyrimidin-2-ylamine as a beige solid (0.91 g, yield: 90%) which was characterized by its mass spectrum as follows: MS (m/z) 225.0 [M+H]+.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dee356fc3ffb48f18ebf074c70b72c36
Source dataset
uspto-grants-2012_03
Patent number
US08143394B2

Reaction notes

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