8-Bromo-6-methylpyrido[4,3-d]pyrimidin-5(6H)-one → US10023592, Example 234

HRID 575703Notes

Reaction equation

HRID 575703 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])=[CH:7][C:6]=1B1OC(C)(C)C(C)(C)O1.C(S(C1C=CC(OCCC)=C(B2OC(C)(C)C(C)(C)O2)C=1)(=O)=O)C.Br[C:55]1[C:60]2[N:61]=[CH:62][N:63]=[CH:64][C:59]=2[C:58](=[O:65])[N:57]([CH3:66])[CH:56]=1.BrC1C2N=C(C3C=NN(C)C=3)N=CC=2C(=O)N(C)C=1>>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH3:15])(=[O:12])=[O:13])=[CH:7][C:6]=1[C:55]1[C:60]2[N:61]=[CH:62][N:63]=[CH:64][C:59]=2[C:58](=[O:65])[N:57]([CH3:66])[CH:56]=1

Participants

5

Reactant 4

HCID 1180219268-Bromo-6-methylpyrido[4,3-d]pyrimidin-5(6H)-oneHCID 1180223108-Bromo-6-methyl-2-(1-methylpyrazol-4-yl)pyrido[4,3-d]pyrimidin-5-oneHCID 1235700892-(5-Ethylsulfonyl-2-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1239594082-[2-(2,4-Difluorophenoxy)-5-ethylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118021443US10023592, Example 234

Procedure

The title compound of step 2 was substituted for the title compound of Example 225, step 2 and the title compound of Example 231, step 3 was substituted for the title compound of Example 224, step 4 and reacted in a similar manner as Example 225, step 3. 1H NMR (CDCl3, 400 MHz) δ 9.60 (s, 1H), 9.27 (s, 1H), 8.12 (s, 1H), 8.02 (d, J=2.0 Hz, 1H), 7.94 (dd, J1=8.8 Hz, J2=2.0 Hz, 1H), 7.32-7.25 (m, 1H), 7.15-7.09 (m, 1H), 7.03-6.97 (m, 2H), 3.70 (s, 3H), 3.27 (q, J=7.6 Hz, 2H), 1.30 (t, J=7.2 Hz, 3H). LCMS: 458.0 (M+H)+

Workup

  1. customreacted in a similar manner as Example 225, step 3

Sources & evidence

ORD record
ord-8e78ac9f28694a07a35b744904b8ccb2
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

Loading…