6-Chloro-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine → HCID 57906751, compound

HRID 2196117Notes

Reaction equation

HRID 2196117 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[C:7]([NH2:17])[N:8]=[C:9](N3C=NC=N3)[C:10]=2[N:11]=1.[CH2:18]([Mg]Br)[CH2:19][CH3:20]>O1CCCC1.CN1CCCC1=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[C:7]([NH2:17])[N:8]=[C:9]([CH2:18][CH2:19][CH3:20])[C:10]=2[N:11]=1

Participants

6

Reactant 2

HCID 576983146-Chloro-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amineHCID 178455851HCID 178455851, compound

Product 1

HCID 57906751HCID 57906751, compound

Reagents, catalysts & solvents 3

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent3×HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a suspension of the intermediate of example 1 (0.47 g, 1.9 mmol) and iron tris(acetylacetonate) (34 mg, 0.095 mmol) in tetrahydrofuran (50 ml, hereinafter THF) and N-methylpyrrolidone (20 ml, hereinafter NMP) was added n-propylmagnesium bromide (1.9 ml, 3.8 mmol as a 2.0 M solution in THF). After stirring at room temperature for 40 minutes, the solution was diluted with THF and then quenched by adding a solution of 1N HCl. The mixture was extracted with ethyl acetate (150 ml), then dried over Na2SO4 and concentrated to afford 6-chloro-4-n-propyl-pyrido[3,2-d]pyrimidin-2-ylamine as a brown solid (0.32 g), which was used in the next step without purification. Its mass spectrum data was as follows: MS (m/z) 223.1 [M+H]+.

Workup

  1. customquenched
  2. additionby adding a solution of 1N HCl
  3. extractionThe mixture was extracted with ethyl acetate (150 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0893a91e2384da896931e78fbcabe7d
Source dataset
uspto-grants-2012_12
Patent number
US08338435B2

Reaction notes

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