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

HRID 2387868Notes

Reaction equation

HRID 2387868 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.[Sn](C)(C)(C)[CH3:18]>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]([CH3:18])[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

To the product from step (i) (20 g) in DMF (200 ml), Pd(PPh3)4 (2 g) was added followed by SnMe4 (20 ml) and the mixture heated at 100° C. for 16 h. The solvent was evaporated and the residue partitioned between EtOAc and brine, the organics were dried and solvent removed. The product was purified by silica chromatography to give the subtitle compound, 14.4 g.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between EtOAc and brine
  3. customthe organics were dried
  4. customsolvent removed
  5. customThe product was purified by silica chromatography

Sources & evidence

ORD record
ord-8fa53d4e22fc42f192123ba6d5c57e96
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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