Isopropanol → 6-Chloro-4-[(propan-2-yl)oxy]pyrido[3,2-d]pyrimidin-2-amine

HRID 1099110Notes

Reaction equation

HRID 1099110 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[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.CC(O)C>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:4][CH:2]([CH3:3])[CH3:1])[C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 23665647Potassium tert-butoxideHCID 576983146-Chloro-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine

Product 1

HCID 580198016-Chloro-4-[(propan-2-yl)oxy]pyrido[3,2-d]pyrimidin-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Potassium tert-butoxide (4.0 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 (1.0 g) and 2-propanol (0.313 mL) in DCM (50 mL). After stirring at room temperature for 30 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-propoxy)-pyrido[3,2-d]pyrimidin-2-ylamine as a yellow solid (0.65 g, yield: 67%) which was characterized by its mass spectrum as follows: MS (m/z) 239.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a22d3f1f7cbb4ad0a3dee6584612aa7f
Source dataset
uspto-grants-2012_03
Patent number
US08143394B2

Reaction notes

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