3-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-pyrazin-2-ylaminomethyloxazolidin-2-one → tert-Butyl pyrimidin-2-ylcarbamate

HRID 8181Notes

Reaction equation

HRID 8181 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C@@H](CO)C(N1CCC(C2C(F)=CC(N3C[C@H](CNC4C=NC=CN=4)OC3=O)=CC=2F)=CC1)=O>>[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][CH:12]=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 207256613-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-pyrazin-2-ylaminomethyloxazolidin-2-oneHCID 220145442-(Di-(t-butoxycarbonyl)amino)pyrimidine

Product 1

HCID 10976384tert-Butyl pyrimidin-2-ylcarbamateYield 93.1%

Procedure

2-(Di-(t-butoxycarbonyl)amino)pyrimidine (5.2 g, 17.6 mM) was hydrolysed by essentially the technique for the appropriate intermediate of Example 22 to give the title product as a white solid (3.2 g). NMR (DMSO-d6) δ: 1.43 (s, 9H); 7.08 (t, 1H); 8.57 (d, 2H); 9.91 (s, 1H). MS (ESP): 196 (MH+) for C9H13N3O2

Sources & evidence

ORD record
ord-de80b7472ee04bd9950c8d3bee94cb3e
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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