Potassium Phosphate, Tribasic → 2-chloro-5-(1-(4-chlorophenyl)cyclopropyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

HRID 2169564Notes

Reaction equation

HRID 2169564 reaction equation
Br[C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:17][C:18]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:20][CH2:19]2)=[O:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(O)(C)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:5]1[N:6]=[CH:7][C:2]2[N:17]([C:18]3([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[CH2:20][CH2:19]3)[C:15](=[O:16])[CH:10]3[CH2:11][O:12][CH2:13][CH2:14][N:9]3[C:3]=2[N:4]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866701104-(5-bromo-2-chloropyrimidin-4-yl)-N-(1-(4-chlorophenyl)cyclopropyl)morpholine-3-carboxamide

Product 1

HCID 866701122-chloro-5-(1-(4-chlorophenyl)cyclopropyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x35 using 4-(5-bromo-2-chloropyrimidin-4-yl)-N-(1-(4-chlorophenyl)cyclopropyl)morpholine-3-carboxamide (PREPARATION x33, 300 mg, 0.635 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (27.6 mg, 0.048 mmol), palladium(II) acetate (7.13 mg, 0.032 mmol), and potassium phosphate, tribasic (189 mg, 0.890 mmol) in dioxane (2.5 mL) and tert-butanol (0.5 mL). ESI-MS m/z [M+H]+ calc'd for C19H17Cl2N3O2, 391.07; found 391.0.

Sources & evidence

ORD record
ord-a9a75061b3fb4d2ebb37bac00b6b34ff
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

Loading…