4-(Carbamoylamino)benzeneboronic acid, pinacol ester → (S)-1-(4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626588Notes

Reaction equation

HRID 1626588 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:5]2[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH2:36])=[O:35])=[CH:29][CH:28]=2)O1>>[CH3:11][N:9]1[CH2:10][C:5]2[C:4]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]3[CH3:18])=[N:3][C:2]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH2:36])=[O:35])=[CH:29][CH:28]=3)=[N:7][C:6]=2[CH2:8]1

Participants

3

Reactant 2

HCID 167274404-(Carbamoylamino)benzeneboronic acid, pinacol esterHCID 86663154(S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 46912891(S)-1-(4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

Procedure

Method as intermediate 5 using (S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 12) and 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea as starting materials.

Sources & evidence

ORD record
ord-0155e27d8a014574b89c87a196f3d913
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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