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Cesium carbonate → tert-butyl (3R)-3-[[6-methoxy-5-(5-methyl-1,3-benzothiazol-2-yl)-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

HRID 1507528
Notes
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Reaction equation

HRID 1507528 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.I[C:12]1[C:13]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)=[N:14][C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:16][C:17]=1[O:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:19][O:18][C:17]1[N:16]=[C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:14]=[C:13]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)[C:12]=1[C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 143445645-Methyl-1,3-benzothiazoleHCID 89554305(R)-Tert-butyl 3-(5-iodo-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

Product 1

HCID 117683808tert-butyl (3R)-3-[[6-methoxy-5-(5-methyl-1,3-benzothiazol-2-yl)-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure as in step 3 of Example 337 using 5-methyl-1,3-benzothiazole (52.2 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100.0 mg, 0.19 mmol, 1.00 equiv), cesium Carbonate (0.37 g, 6.00 equiv), Pd(PPh3)4 (40.4 mg, 0.03 mmol, 0.18 equiv) and copper (I) iodide (6.7 mg, 0.09 mmol, 0.18 equiv) in DMF (6 mL). The crude product was purified by chromatography on a silica gel column eluting with petroleum ether/ethyl acetate (15:1-3:1) to afford the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 541.

Workup

  1. customThe crude product was purified by chromatography on a silica gel column
  2. washeluting with petroleum ether/ethyl acetate (15:1-3:1)

Sources & evidence

ORD record
ord-6d98038da51c483aa7e123791fa485f0
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221809B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes