Sodium ethoxide → 6-Chloro-4-ethoxypyrido[3,2-d]pyrimidin-2-amine

HRID 1099109Notes

Reaction equation

HRID 1099109 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]([NH2:21])[N:12]=[C:13](N3C=NC=N3)[C:14]=2[N:15]=1>C1COCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]([NH2:21])[N:12]=[C:13]([O:1][CH2:2][CH3:3])[C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 576983146-Chloro-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine

Product 1

HCID 597672176-Chloro-4-ethoxypyrido[3,2-d]pyrimidin-2-amineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium ethoxide (2.2 mL; 21 wt % in ethanol) was added to a suspension of 6-chloro-4-[1,2,4]triazol-1-yl-pyrido[3,2-d]pyrimidin-2-ylamine (1 g) in THF (50 mL). After stirring at room temperature for 30 minutes, THF was removed in vacuo and the residue was diluted with ethyl acetate (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford 6-chloro-4-ethoxy-pyrido[3,2-d]pyrimidin-2-ylamine as a beige solid (0.71 g, yield: 79%) which was characterized by its mass spectrum as follows: MS (m/z) 225.0 [M+H]+.

Workup

  1. customTHF was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ca786c5bfa34463bfe681a90590b011
Source dataset
uspto-grants-2012_03
Patent number
US08143394B2

Reaction notes

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