Cesium carbonate → HCID 66841464, compound

HRID 533456Notes

Reaction equation

HRID 533456 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([C:17]([NH2:19])=[O:18])=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]([N:30]2[CH2:34][CH:33]=[CH:32][CH2:31]2)=[O:29])[CH:24]=[CH:25][CH:26]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:30]1([C:28]([NH:27][C:23]2[CH:22]=[C:21]([NH:20][C:2]3[N:7]=[C:6]([NH:8][C@@H:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH3:10])[C:5]([C:17]([NH2:19])=[O:18])=[CH:4][N:3]=3)[CH:26]=[CH:25][CH:24]=2)=[O:29])[CH2:34][CH:33]=[CH:32][CH2:31]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 58098631HCID 58098631, compoundHCID 58098669HCID 58098669, compound

Product 1

HCID 66841464HCID 66841464, compoundYield 22.5%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 2-chloro-4-(1-phenylethylamino)pyrimidine-5-carboxamide (2, 27 mg, 0.1 mmoles), N-(3-aminophenyl)-2,5-dihydro-1H-pyrrole-1-carboxamide (3, 34 mg, 0.15 mmoles), Pd(OAc)2 (2 mg). BINAP (15 mg), Cs2CO3 (100 mg) in dioxane (1 mL) was heated at 120° C. under microwave for 60 min. Purification with reversed phase HPLC, (R)-2-(3-(2,5-dihydro-1H-pyrrole-1-carboxamido)phenylamino)-4-(1-phenylethylamino)pyrimidine-5-carboxamide (4, 10 mg) was obtained. MS found for C24H25N7O2 as (M+H)+ 444. UV: λ=248 nm. 1H NMR: (CD3OD) δ 8.35 (s, 1H), 7.85 (s, 1H), 7.3 (m, 4H), 7.2 (m, 3H), 7.05 (d, 1H), 5.95 (s, 2H), 5.4 (dd, 1H), 4.25 (s, 4H), 1.48 (d, 3H).

Workup

  1. customPurification with reversed phase HPLC

Sources & evidence

ORD record
ord-c0e21f97d2ad4f55890efc367b99e16d
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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