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

HRID 2215729Notes

Reaction equation

HRID 2215729 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-f24d1f03c3f149859639fb85c4820158
Source dataset
uspto-grants-2006_09
Patent number
US07109333B2

Reaction notes

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