2-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol → 2-(1-((2-(2-Methylbenzofuran-3-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 1043564Notes

Reaction equation

HRID 1043564 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[CH3:18])O1.Cl[C:21]1[N:22]=[C:23]([N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)[C:24]2[N:30]=[C:29]([CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([C:38]([OH:41])([CH3:40])[CH3:39])[CH2:34][CH2:33]3)[CH:28]=[CH:27][C:25]=2[N:26]=1>>[CH3:18][C:10]1[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:9]=1[C:21]1[N:22]=[C:23]([N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)[C:24]2[N:30]=[C:29]([CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([C:38]([OH:41])([CH3:40])[CH3:39])[CH2:34][CH2:33]3)[CH:28]=[CH:27][C:25]=2[N:26]=1

Participants

3

Reactant 2

HCID 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-olHCID 673417654,4,5,5-Tetramethyl-2-(2-methylbenzofuran-3-yl)-1,3,2-dioxaborolane

Product 1

HCID 533779502-(1-((2-(2-Methylbenzofuran-3-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Procedure

Following General Procedure A, 4,4,5,5-tetramethyl-2-(2-methylbenzofuran-3-yl)-1,3,2-dioxaborolane and 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 were reacted to give 103. LCMS (MH+)=502.3. 1H-NMR (DMSO-d6): δ 8.55 (m, 1H), 8.19 (d, 1H), 7.86 (d, 1H), 7.56 (m, 1H), 7.32 (m, 2H), 4.48 (s, 4H), 4.01 (s, 1H), 3.85 (m, 4H), 3.72 (s, 2H), 2.96 (s, 3H), 2.93 (m, 2H), 2.01 (m, 2H), 1.66 (m, 2H), 1.29 (m, 2H), 1.25 (m, 1H), 1.04 (s, 6H)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d2599322985945eba775550de569103e
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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