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

HRID 1517459Notes

Reaction equation

HRID 1517459 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 t-butoxide (4 mL, 4 mmol; 1 M in THF) was added to a suspension mixture of 6-chloro-4-[1,2,4]triazol-1-yl-pyrido[3,2-d]pyrimidin-2-ylamine (1 g, 4 mmol) and 2-methoxyethanol (0.32 mL, 4 mmol) 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 the pure title compound as a beige solid (0.91 g, yield 90%) which was characterised 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-68428d243fe846e992ebb25473db4967
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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