Cesium carbonate → 10-Chloro-2-(cyclopropylmethyl)-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

HRID 2234397Notes

Reaction equation

Br[C:2]1[C:3]([N:9]([CH2:16][CH:17]2[CH2:19][CH2:18]2)[CH2:10][CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:5]1[N:4]=[C:3]2[C:2]([N:14]([CH3:15])[C:12](=[O:13])[CH2:11][CH2:10][N:9]2[CH2:16][CH:17]2[CH2:19][CH2:18]2)=[CH:7][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a partial solution of 3-[(5-bromo-2-chloro-pyrimidin-4-yl)-(cyclopropylmethyl)amino]-N-methyl-propanamide (Intermediate 94; 426 mg, 1.18 mmol) in anhydrous 1,4-dioxane (15 mL) was added Caesium Carbonate (790 mg, 2.42 mmol). Nitrogen was bubbled through the reaction mixture for 10 minutes, prior to addition of Tris(dibenzylideneacetone)dipalladium(0) (69 mg, 0.075 mmol) and XANTPHOS (62 mg, 0.107 mmol). The reaction was heated to 100° C. and stirred under nitrogen for 18 hrs.

Workup

customNitrogen was bubbled through the reaction mixture for 10 minutes

Sources & evidence

ORD record: ord-062c1f4b01914fcfa9c9678934437a22
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709471B2

Reaction notes

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