1-(5-Methylisoxazol-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-(4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)-3-(5-methylisoxazol-3-yl)urea

HRID 1626589Notes

Reaction equation

HRID 1626589 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.[CH3:19][C:20]1[O:24][N:23]=[C:22]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=2)=[O:27])[CH:21]=1>>[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:32]3[CH:33]=[CH:34][C:29]([NH:28][C:26]([NH:25][C:22]4[CH:21]=[C:20]([CH3:19])[O:24][N:23]=4)=[O:27])=[CH:30][CH:31]=3)=[N:7][C:6]=2[CH2:8]1

Participants

3

Reactant 2

HCID 666874601-(5-Methylisoxazol-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 86663154(S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 46912892(S)-1-(4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)-3-(5-methylisoxazol-3-yl)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-(5-methylisoxazol-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 15) as starting materials.

Sources & evidence

ORD record
ord-5f0a9bf4362547aea0491adb2e6f7fb1
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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