2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine → tert-butyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

HRID 2353699Notes

Reaction equation

HRID 2353699 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]([C:16]1[S:17][C:18]([Sn](CCCC)(CCCC)CCCC)=[CH:19][N:20]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])[CH3:3].Cl[C:35]1[N:40]=[C:39]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][C@@H:42]2[CH3:47])[CH:38]=[C:37]([CH2:48][S:49]([CH3:52])(=[O:51])=[O:50])[N:36]=1>C1(C)C=CC=CC=1.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>[CH3:47][C@H:42]1[CH2:43][O:44][CH2:45][CH2:46][N:41]1[C:39]1[CH:38]=[C:37]([CH2:48][S:49]([CH3:52])(=[O:51])=[O:50])[N:36]=[C:35]([C:18]2[S:17][C:16]([N:8]([C:9]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:15])[C:6](=[O:7])[O:5][C:2]([CH3:4])([CH3:1])[CH3:3])=[N:20][CH:19]=2)[N:40]=1

Participants

5

Reactant 2

HCID 575473562-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidineHCID 59380135tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(5-tributylstannyl-1,3-thiazol-2-yl)carbamate

Product 1

HCID 59477211tert-butyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamateYield 93.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(5-tributylstannyl-1,3-thiazol-2-yl)carbamate (3 g, 5.1 mmol), 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine (1 g, 3.2 mmol) and palladium tetrakis (triphenylphosphine) (50 mg), in toluene (10 mL) was heated at 105° C. for 2 hours under nitrogen. The mixture was chromatographed on silica to give the desired material (1.7 g).

Workup

  1. customThe mixture was chromatographed on silica

Sources & evidence

ORD record
ord-228e176820534c909a7f66bd87f3a69e
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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