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

HRID 458111Notes

Reaction equation

HRID 458111 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-f6d1c34a165641378012b4ba71571354
Source dataset
uspto-grants-2007_03
Patent number
US07189734B2

Reaction notes

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