2-Chloro-4-methylpyrimidine → HCID 57671639, compound

HRID 553521Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=2)[N:5]([CH3:21])[C:4](=[O:22])[C:3]=1[C:23]([NH:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[O:24].Cl[C:35]1[N:40]=[C:39]([CH3:41])[CH:38]=[CH:37][N:36]=1>>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([C:35]3[N:40]=[C:39]([CH3:41])[CH:38]=[CH:37][N:36]=3)[CH:10]=2)[N:5]([CH3:21])[C:4](=[O:22])[C:3]=1[C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24]

Participants

Reactant 2

HCID 116296072-Chloro-4-methylpyrimidine

HCID 57671682HCID 57671682, compound

Product 1

HCID 57671639HCID 57671639, compound

Procedure

The title compound was prepared from tert-butyl 2-(4-hydroxy-1-methyl-2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetate (Example 26 (h)) and 2-chloro-4-methylpyrimidine analogously to the procedures described for the preparation of Example 26 (i) and Example 26 (k), or Example 21 (b). MS (ESI, pos. ion) m/z: 370 (M+1). 1NMR (400 MHz, DMSO-d6) δ ppm: 10.41 (s, 1 H), 9.65 (s, 1 H), 9.24 (s, 1 H), 8.80 (d, J=4.9 Hz, 1 H), 7.41 (d, J=4.9 Hz, 1 H), 4.13 (d, J=5.3 Hz, 2 H), 3.74 (s, 3 H), 2.59 (s, 3 H).

Sources & evidence

ORD record: ord-f65c14e3cac040d9b92ab448e9b370a5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048892B2

Reaction notes

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