3-(1,3-Dioxolan-2-yl)-phenyl-tributylstannane → (4-Benzyloxy-phenyl)-(6-(3-(1,3-dioxolan-2-yl)-phenyl)-pyrido[3,4-d]pyrimidin-4-yl)-amine

HRID 51144Notes

Reaction equation

HRID 51144 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[CH:25]=[C:24](Cl)[N:23]=[CH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:27]1[CH2:31][CH2:30][O:29][CH:28]1[C:32]1[CH:33]=[C:34]([Sn](CCCC)(CCCC)CCCC)[CH:35]=[CH:36][CH:37]=1>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[CH:25]=[C:24]([C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([CH:28]5[O:27][CH2:31][CH2:30][O:29]5)[CH:33]=4)[N:23]=[CH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 152549343-(1,3-Dioxolan-2-yl)-phenyl-tributylstannaneHCID 219521684-(4-Benzyloxyanilino)6-chloropyrido[3,4-d]pyrimidine

Product 1

HCID 22725131(4-Benzyloxy-phenyl)-(6-(3-(1,3-dioxolan-2-yl)-phenyl)-pyrido[3,4-d]pyrimidin-4-yl)-amineYield 13.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(4-Benzyloxy-phenyl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (1.4 g) and 3-(1,3-dioxolan-2-yl)-phenyl-tributylstannane (3.08 g) [A. Lee and W-C. Dai, Tetrahedron (1997), 53(3), 859-868] in dioxan (30 ml) were reacted together as in Procedure B. The mixture was evaporated and the residue suspended in dichloromethane. This was then filtered through celite and the solvent evaporated. The gummy residue was then triturated with hexane giving a beige solid. This material was further purified by column chromatography, giving a brown foam (252 mg); m/z 477 (M+1)+.

Workup

  1. customThe mixture was evaporated
  2. filtrationThis was then filtered through celite
  3. customthe solvent evaporated
  4. customThe gummy residue was then triturated with hexane giving a beige solid
  5. customThis material was further purified by column chromatography

Sources & evidence

ORD record
ord-238eb57abbf748bb8dc0e33ebc47f885
Source dataset
uspto-grants-2004_03
Patent number
US06713485B2

Reaction notes

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