Tetramethyltin → 2-Amino-4-methyl-6-(pentylamino)pyrimidine-5-carbaldehyde

HRID 1617195Notes

Reaction equation

HRID 1617195 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH:9]=[O:10])=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:3]=1.[CH3:17][Sn](C)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([CH3:17])[C:5]([CH:9]=[O:10])=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:3]=1

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 866334062-Amino-4-chloro-6-(pentylamino)pyrimidine-5-carbaldehyde

Product 1

HCID 866334072-Amino-4-methyl-6-(pentylamino)pyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from step (i) (20 g), tetramethyltin (20 ml) and tetrakis(triphenylphosphine)palladium (0) (2 g) in DMF (200 ml) was heated at 100° C. for 16 h then evaporated under reduced pressure. The residue was partitioned between EtOAc/brine, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 50-60% EtOAc/isohexane to afford the subtitle compound, 14.4 g.

Workup

  1. customthen evaporated under reduced pressure
  2. customThe residue was partitioned between EtOAc/brine
  3. customthe organics separated, dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 50-60% EtOAc/isohexane

Sources & evidence

ORD record
ord-68eec780c2704f11afe8b38953fceb1d
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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