Nitrogen → HCID 136061319, compound

HRID 1093117Notes

Reaction equation

C([O:4][C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)[N:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C=C.N#N>C(O)CC.[Rh](Cl)(Cl)Cl>[CH2:25]([O:24][C:6]1[C:5](=[O:4])[NH:10][C:9]([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][OH:18])[CH2:15][CH2:16]2)=[N:8][C:7]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of ethyl 6-(allyloxy)-5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)pyrimidine-4-carboxylate (1.206 g, 2.82 mmol) in n-propanol (10 mL) was sparged with N2. Rhodium(III) chloride (0.030 g, 0.141 mmol) was added and the resulting mixture was stirred overnight at 100° C. The mixture was cooled to room temperature and partitioned between water and CH2Cl2. The organic phase was dried (Na2SO4), filtered and concentrated to give a yellow solid that was triturated with Et2O. The product was collected by filtration to give the title compound as a white solid (0.8252 g, 76% yield). 1H NMR (300 MHz, CDCl3) δ: 7.43 (2H, d, J=7.3 Hz), 7.37-7.29 (3H, m), 5.05 (2H, s), 4.46 (2H, d, J=13.1 Hz), 4.31 (2H, q, J=7.1 Hz), 3.44 (2H, d, J=5.8 Hz), 2.94-2.88 (2H, m), 1.74 (2H, d, J=13.1 Hz), 1.73-1.66 (1H, m), 1.29 (3H, t, J=7.2 Hz), 1.28-1.22 (2H, m). LCMS (M+H) calcd for C20H26N3O5: 388.18; found: 388.23.

Workup

temperatureThe mixture was cooled to room temperature
custompartitioned between water and CH2Cl2
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customto give a yellow solid
customthat was triturated with Et2O
filtrationThe product was collected by filtration

Sources & evidence

ORD record: ord-48a5766791e64aa1baa7066b2bde0cac
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129398B2

Reaction notes

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