2-(Tributylstannyl)furan-4-carboxaldehyde → 5-(4-(4-(3-Fluorobenzyloxy)-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl)-furan-3-carbaldehyde

HRID 51140Notes

Reaction equation

HRID 51140 reaction equation
Cl[C:2]1[N:27]=[CH:26][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=4)=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:33]1[O:37][CH:36]=[C:35]([CH:38]=[O:39])[CH:34]=1)CCC>O1CCOCC1>[F:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:9]2[C:4]3[CH:3]=[C:2]([C:33]4[O:37][CH:36]=[C:35]([CH:38]=[O:39])[CH:34]=4)[N:27]=[CH:26][C:5]=3[N:6]=[CH:7][N:8]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 109599912-(Tributylstannyl)furan-4-carboxaldehydeHCID 21952062(6-Chloropyrido[3,4-d]pyrimidin-4-yl)-(4-(3-fluorobenzyloxy)-phenyl)-amine

Product 1

HCID 219520885-(4-(4-(3-Fluorobenzyloxy)-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl)-furan-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(6-Chloropyrido[3,4-d]pyrimidin-4-yl)-(4-(3-fluorobenzyloxy)-phenyl)-amine (1 g) and 5-(tributylstannyl)-furan-3-carbaldehyde (J. Org. Chem. (1992), 57(11), 3126-31) (1.84 g) in dioxan (35 ml) were reacted together as in Procedure B. The solvent was evaporated and the residue suspended in dichloromethane. The mixture was filtered through Celite® and then evaporated. The residue was triturated with hexane giving a beige solid (1 g); m/z 441 (M+1)+.

Workup

  1. customThe solvent was evaporated
  2. filtrationThe mixture was filtered through Celite®
  3. customevaporated
  4. customThe residue was triturated with hexane giving a beige solid (1 g)

Sources & evidence

ORD record
ord-a3818ff015a647a18eff43dbca56e84e
Source dataset
uspto-grants-2004_03
Patent number
US06713485B2

Reaction notes

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