HCID 57474771, compound → HCID 57474769, compound

HRID 2428025Notes

Reaction equation

HRID 2428025 reaction equation
[NH2:1][C:2]1[C:3]([C:35](OC)=[O:36])=[N:4][C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][Si](C(C)C)(C(C)C)C(C)C)[CH:19]=2)=[N:6][C:7]=1[NH:8][CH:9]1[C:17]2[C:12](=CC=C[CH:16]=2)CC1.[NH2:39]C1C(C(OC)=O)=NC(Cl)=NC=1NCC(C)C.C([Si](C(C)C)(C(C)C)[O:60][C:61]1C=CC=C([Sn](C)(C)C)C=1)(C)C>CN(C)C=O>[OH:24][C:20]1[CH:19]=[C:18]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:61](=[O:60])[N:8]3[CH2:9][CH:17]([CH3:12])[CH3:16])=[C:3]([C:35]([NH2:39])=[O:36])[N:4]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 57474771HCID 57474771, compoundHCID 68961932HCID 68961932, compoundHCID 86627727HCID 86627727, compound

Product 1

HCID 57474769HCID 57474769, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 5-amino-6-(2,3-dihydro-1H-inden-1-ylamino)-2-(3-(triisopropylsilyloxy)phenyl)pyrimidine-4-carboxylate. Methyl 5-amino-2-chloro-6-(isobutylamino)pyrimidine-4-carboxylate. (0.285 g, 1.11 mmol) triisopropyl(3-(trimethylstannyl)phenoxy)silane (0.691 g, 1.67 mmol) and bisdichloro(triphenylphosphine) palladium (0) (0.311 g, 0.444 mmol) were combined in dimethyl formamide (4 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 using Biotage chromatography (0 to 40% EtOAc in hexanes) to afford the title compound (0.300 g, 58%). MS (ESI) m/z 473.6 [M+1]+.

Workup

  1. customOnce starting materials were consumed
  2. customcondensed under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-54fdd19867224735952fd6d83d1c5945
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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