HCID 57474817, compound → HCID 57474820, compound

HRID 391703Notes

Reaction equation

HRID 391703 reaction equation
[NH2:1][C:2]1[C:3]([C:40](OC)=[O:41])=[N:4][C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:17]=2)=[N:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[NH2:44]C1C(C(OC)=O)=NC(Cl)=NC=1NCC1CCOCC1.C([Si](C(C)C)(C(C)C)[O:68][C:69]1C=CC=C([Sn](C)(C)C)C=1)(C)C>CN(C)C=O>[OH:22][C:18]1[CH:17]=[C:16]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:69](=[O:68])[N:8]3[CH2:9][CH:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[C:3]([C:40]([NH2:44])=[O:41])[N:4]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 57474817HCID 57474817, compoundHCID 86627727HCID 86627727, compoundHCID 86627730HCID 86627730, compound

Product 1

HCID 57474820HCID 57474820, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 5-amino-2-(3-(tert-butyldiphenylsilyloxy)phenyl)-6-((tetrahydro-2H-pyran-4-yl)methylamino)pyrimidine-4-carboxylate. Methyl 5-amino-2-chloro-6-((tetrahydro-2H-pyran-4-yl)methylamino)pyrimidine-4-carboxylate. (0.400 g, 1.33 mmol) triisopropyl(3-(trimethyl-stannyl)phenoxy)silane (0.772 g, 1.86 mmol) and bisdichloro(triphenylphosphine)palladium (0) (0.280 g, 0.400 mmol) were combined in dimethyl formamide (6 mL) and heated to 100° C. The reaction was monitored via thin layer chromatography. Once starting materials were consumed, the solution was condensed under reduced pressure and purified via Biotage chromatography (0-50% EtOAc in hexanes) to afford the title compound (0.276 g, 40%). MS (ESI) m/z 515.6 [M+1]+.

Workup

  1. customOnce starting materials were consumed
  2. customcondensed under reduced pressure
  3. custompurified via Biotage chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-66b6c1d59efb47ccad83b0082486a82c
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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