HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2169568
Notes
Print preview

Reaction equation

HRID 2169568 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]([Cl:27])[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]([Cl:27])[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
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866701154-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-chloro-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

Product 1

HCID 866701162-chloro-5-(6-chloro-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) acetateCatalyst
HCID 6386tert-ButanolSolvent
HCID 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-chloro-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide (PREPARATION x40, 567 mg, 1.201 mmol), Xantphos (52.1 mg, 0.090 mmol), palladium(II) acetate (13.48 mg, 0.060 mmol) and potassium phosphate (255 mg, 1.201 mmol) in dioxane (5 mL) and tert-butanol (1 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.21-2.48 (m, 3 H), 2.87-3.05 (m, 2 H), 3.05-3.21 (m, 1 H), 3.47-3.65 (m, 2 H), 3.88-4.01 (m, 1 H), 4.08-4.32 (m, 2 H), 4.39-4.56 (m, 1 H), 7.16-7.42 (m, 4 H). ESI-MS m/z [M+H]+ calc'd for C18H16Cl2N4O2, 391.07; found 391.3.

Sources & evidence

ORD record
ord-2dee65419ac646e79f3f905bf02ba11a
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09045496B2

Reaction notes

Loading…

On this pageParticipantsProcedureSources & evidenceReaction notes