Cesium carbonate → Tert-butyl 3-(6-methoxy-5-(7-methylbenzo[d]thiazol-2-yl)-2-morpholino-1,6-dihydropyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 1507527Notes

Reaction equation

HRID 1507527 reaction equation
I[C:2]1[CH:7]([O:8][CH3:9])[NH:6][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:3]=1[NH:16][C@@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.[CH3:30][C:31]1[C:39]2[S:38][CH:37]=[N:36][C:35]=2[CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.I[Cu]>[CH3:9][O:8][CH:7]1[NH:6][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:3]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[C:2]1[C:37]1[S:38][C:39]2[C:31]([CH3:30])=[CH:32][CH:33]=[CH:34][C:35]=2[N:36]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 156550227-Methylbenzo[d]thiazoleHCID 178494221tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate

Product 1

HCID 178494220Tert-butyl 3-(6-methoxy-5-(7-methylbenzo[d]thiazol-2-yl)-2-morpholino-1,6-dihydropyrimidin-4-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Following the same procedure as in step 3 of Example 337 using tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate (30 mg, 0.06 mmol, 1.00 equiv), 7-methyl-1,3-benzothiazole (15.5 mg, 0.10 mmol, 1.81 equiv), tetrakis(triphenylphosphane) palladium (12 mg, 0.01 mmol, 0.18 equiv), iodocopper (2 mg, 0.01 mmol, 0.18 equiv), and cesium Carbonate (112.8 mg, 0.35 mmol, 6.00 equiv) in N,N-dimethylformamide (2.5 mL). The crude product was purified through a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to afford the title compound as a brown solid.

Workup

  1. customThe crude product was purified through a silica gel column with ethyl acetate/petroleum ether (1:10-1:5)

Sources & evidence

ORD record
ord-2bed66162564450595ec942986e6eece
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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