1,4-Dioxane → (1-Benzyl-1H-indazol-5-yl)-(6-(5-[1,3-dioxolan-2-yl]-furan-2-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine

HRID 566393

Reaction equation

HRID 566393 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26](Cl)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)C1O[C:36]([CH2:39][CH:40]2[O:44][CH2:43][CH2:42][O:41]2)=[CH:37][CH:38]=1)CCC.[O:53]1CCOCC1>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26]([C:38]5[O:53][C:39]([CH:40]6[O:41][CH2:42][CH2:43][O:44]6)=[CH:36][CH:37]=5)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 21952012(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amineHCID 227274162-(Tributylstannyl)-5-(1,3-dioxolan-2-ylmethyl)-furan

Product 1

HCID 21951893(1-Benzyl-1H-indazol-5-yl)-(6-(5-[1,3-dioxolan-2-yl]-furan-2-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)Catalyst

Procedure

(1-Benzyl-1H-indazol-5-yl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (4.28 g), 2-(tributylstannyl)-5-(1,3-dioxolan-2-ylmethyl)-furan (J. Chem Soc., Chem. commun., (1988), p560) (10 g) and 1,4-bis(diphenylphosphino)butane palladium (II) chloride (1 g) were heated at reflux in dioxane (150 ml) for 24 hr (Procedure B). The solvent was removed in vacuo and the residue chromatographed on silica. Subsequent trituration gave the title compound as a yellow solid: δH [2H6]-DMSO 10.46 (1H,s), 9.17 (1H,s), 8.74 (1H,s), 8.52 (1H,s), 8.23 (1H,s), 8.18 (1H,s), 7.80-7.68 (2H,m), 7.41-7.22 (5H,m), 7.17 (1H,d), 6.80 (1H,d), 6.06 (1H,s), 5.71 (2H,s), 4.20-3.96 (4H,m).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-3be8eb624114482c9c5768dbef392f0c
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Linked notes

Loading…