Morpholine → 2,4-Bis(4-methoxybenzyloxy)-7-morpholin-4-ylquinazoline

HRID 2274139Notes

Reaction equation

HRID 2274139 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[N:13][C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:15]2)=[CH:10][CH:9]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][O:18][C:14]2[N:13]=[C:12]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:11]3[C:16](=[CH:17][C:8]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:9][CH:10]=3)[N:15]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 674015107-Bromo-2,4-bis(4-methoxybenzyloxy)quinazoline

Product 1

HCID 674014182,4-Bis(4-methoxybenzyloxy)-7-morpholin-4-ylquinazolineYield 102.1%

Reagents, catalysts & solvents 2

HCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, 2.26 g (2.47 mmol) of tris(dibenzylideneacetone)dipalladium-(0) and 4.42 g (12.35 mmol) of 2-(dicyclohexylphosphino)biphenyl were dissolved in 1.5 l of toluene, and 215.2 ml (2.47 mol) of morpholine and 269.0 g (0.5 mol) of 7-bromo-2,4-bis(4-methoxybenzyloxy)quinazoline [dissolved in 5 l of toluene] were added successively. 66.47 g (0.7 mol) of sodium tert-butoxide were subsequently added in portions, and the mixture was stirred at 90° C. for 12 h. Conventional work-up gave 249.0 g of 2,4-bis(4-methoxybenzyloxy)-7-morpholin-4-ylquinazoline; HPLC/MS (M+H)+=488 as oil [crude product; was reacted further directly].

Sources & evidence

ORD record
ord-fa16cdfe8c7649c5b765502cfbafbcdd
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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