3-[(1-Methylpyrazol-4-yl)methyl]-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-[4-[4-(hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea

HRID 2353709Notes

Reaction equation

HRID 2353709 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]2[CH3:16])[N:3]=1.[CH3:17][N:18]1[CH:22]=[C:21]([CH2:23][NH:24][C:25](=[O:42])[NH:26][C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=2)[CH:20]=[N:19]1>>[OH:9][CH2:8][C:6]1[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]2[CH3:16])[N:3]=[C:2]([C:30]2[CH:31]=[CH:32][C:27]([NH:26][C:25]([NH:24][CH2:23][C:21]3[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=3)=[O:42])=[CH:28][CH:29]=2)[N:7]=1

Participants

3

Reactant 2

HCID 593800143-[(1-Methylpyrazol-4-yl)methyl]-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 59380181[2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanol

Product 1

HCID 593798741-[4-[4-(hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea

Procedure

The preparations of [2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanol (1.00 g, 4.10 mmol) and 3-[(1-methylpyrazol-4-yl)methyl]-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea were described earlier.

Sources & evidence

ORD record
ord-1c4642ef744e4c86879b0f303588aade
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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