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

HRID 1617216Notes

Reaction equation

HRID 1617216 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 partitoned 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. dry with materialthe residue partitoned between EtOAc and brine, the organics were dried
  3. customsolvent removed
  4. customThe product was purified by silica chromatography

Sources & evidence

ORD record
ord-d7d5277a73fa4fdd8b0c24e541551675
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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