HCID 57474801, compound → HCID 57474812, compound

HRID 391700Notes

Reaction equation

HRID 391700 reaction equation
[NH2:1][C:2]1[C:3]([C:39](OC)=[O:40])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)=[N:6][C:7]=1[NH:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[NH2:43]C1C(C(OC)=O)=NC(Cl)=NC=1NC1CCOCC1.C([Si](C(C)C)(C(C)C)[O:66][C:67]1C=CC=C([Sn](C)(C)C)C=1)(C)C>CN(C)C=O>[OH:21][C:17]1[CH:16]=[C:15]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:67](=[O:66])[N:8]3[CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[C:3]([C:39]([NH2:43])=[O:40])[N:4]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 57474801HCID 57474801, compoundHCID 57474804HCID 57474804, compoundHCID 86627727HCID 86627727, compound

Product 1

HCID 57474812HCID 57474812, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 5-amino-2-(3-(tert-butyldiphenylsilyloxy)phenyl)-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate. Methyl 5-amino-2-chloro-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate. (0.400 g, 1.39 mmol) triisopropyl(3-(trimethylstannyl)phenoxy)silane (0.810 g, 1.95 mmol) and bisdichloro(triphenylphosphine)palladium (0) (0.292 g, 0.410 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 to 50% EtOAc in hexanes) to afford the title compound (0.361 g, 51%). MS (ESI) m/z 501.5 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-46d4c29990484b2a87333f8c187e4f65
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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