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 1403781Notes

Reaction equation

HRID 1403781 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-e6e673d832814405858fd913737ac1a4
Source dataset
uspto-grants-2014_12
Patent number
US08912205B2

Reaction notes

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