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

HRID 2169570Notes

Reaction equation

HRID 2169570 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][CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[CH2:20][CH2:19]2)=[O:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.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]([CH:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=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 866701174-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-methoxy-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

Product 1

HCID 866701182-chloro-5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-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-(6-methoxy-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide (PREPARATION x42, 472 mg, 1.009 mmol), Xantphos (43.8 mg, 0.076 mmol), potassium phosphate (214 mg, 1.009 mmol) and palladium(II) acetate (11.33 mg, 0.050 mmol) in dioxane (5 mL) and tert-butanol (1 mL). ESI-MS m/z [M+H]+ calc'd for C19H19ClN4O3, 387.11; found 387.4.

Sources & evidence

ORD record
ord-0f96d005458743d4b741be2b8773c940
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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