(Z)-1-Ethoxy-2-(tributylstannyl)ethene → HCID 58539161, compound

HRID 1804678Notes

Reaction equation

HRID 1804678 reaction equation
Br[C:2]1[C:3]([NH:25][CH3:26])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])=[CH:11][C:10]=2[O:23][CH3:24])=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[CH:32]=[CH:33][O:34]CC)CCC>C1(C)C=CC=CC=1.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>[CH3:24][O:23][C:10]1[CH:11]=[C:12]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[CH:13]=[CH:14][C:9]=1[NH:8][C:5]1[N:4]=[C:3]([NH:25][CH3:26])[C:2]([C:33](=[O:34])[CH3:32])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 58539140HCID 58539140, compound

Product 1

HCID 58539161HCID 58539161, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (4-(5-bromo-4-(methylamino)pyrimidin-2-ylamino)-3-methoxyphenyl)(morpholino)methanone (100 mg, 0.24 mmol), Pd(PPh3)4 (36 mg, 0.03 mmol) and tributylethoxyvinyltin (0.16 mL, 0.47 mmol) in toluene was stirred in a sealed tube at 110° C. for 1 hour. The reaction mix was filtered and concentrated. The reaction mixture was filtered through a pad of silica gel (eluted with 0-100% EtOAc in heptane) to give the crude product. Purification of the crude product was achieved by reverse phase HPLC (9 mg, 10%). Additional compounds made using the above procedure are shown in Table 4 above.

Workup

  1. additionThe reaction mix
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. filtrationThe reaction mixture was filtered through a pad of silica gel (eluted with 0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-84ed290e8a4b4fa9bba4e036b7a189c3
Source dataset
uspto-grants-2013_01
Patent number
US08354420B2

Reaction notes

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