2-Aminopyrimidine-5-boronic acid, pinacol ester → HCID 53378053, compound

HRID 2091840Notes

Reaction equation

HRID 2091840 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][C:12]([NH2:15])=[N:13][CH:14]=2)O1.Cl[C:18]1[N:19]=[C:20]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[C:21]2[N:27]=[C:26]([CH2:28][N:29]3[CH2:34][CH2:33][CH:32]([C:35]([OH:38])([CH3:37])[CH3:36])[CH2:31][CH2:30]3)[CH:25]=[CH:24][C:22]=2[N:23]=1>>[NH2:15][C:12]1[N:13]=[CH:14][C:9]([C:18]2[N:19]=[C:20]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[C:21]3[N:27]=[C:26]([CH2:28][N:29]4[CH2:34][CH2:33][CH:32]([C:35]([OH:38])([CH3:37])[CH3:36])[CH2:31][CH2:30]4)[CH:25]=[CH:24][C:22]=3[N:23]=2)=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 53378053HCID 53378053, compound

Procedure

Following General Procedure A, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 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 107. LCMS (MH+)=465.3. 1H-NMR (DMSO-d6): δ 8.29 (s, 1H), 8.09 (d, 1H), 7.80 (d, 1H), 7.09 (s, 2H), 4.50 (s, 4H), 4.01 (s, 1H), 3.81 (m, 4H), 3.68 (s, 2H), 2.91 (m, 2H), 1.97 (m, 2H), 1.65 (m, 2H), 1.29 (m, 2H), 1.17 (m, 1H), 1.03 (s, 6H)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-70cdd79a88ad4e999951f075e8424c01
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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