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 1631731Notes

Reaction equation

HRID 1631731 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-610cf126220842a7a12a71cf6d9408c5
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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