1-({3-[(Benzyloxy)methyl]oxetan-3-yl}methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (3-((4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methanol

HRID 2279827Notes

Reaction equation

HRID 2279827 reaction equation
C([O:8][CH2:9][C:10]1([CH2:14][N:15]2[CH:19]=[C:18]([B:20]3[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]3)[CH:17]=[N:16]2)[CH2:13][O:12][CH2:11]1)C1C=CC=CC=1.C(OP(CC1C=CC(NC2N=C(NC3C=CC(C4C=C(C(OC)=O)N(CCCO)C=4)=NC=3C(=O)NC)C(C(F)(F)F)=CN=2)=C(OC)C=1)(O)=O)C>>[CH3:27][C:22]1([CH3:28])[C:23]([CH3:25])([CH3:26])[O:24][B:20]([C:18]2[CH:17]=[N:16][N:15]([CH2:14][C:10]3([CH2:9][OH:8])[CH2:11][O:12][CH2:13]3)[CH:19]=2)[O:21]1

Participants

3

Reactant 2

HCID 678131161-({3-[(Benzyloxy)methyl]oxetan-3-yl}methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 86697760Methyl 4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1-(3-hydroxypropyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 67813981(3-((4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methanolYield 95.3%

Procedure

1-({3-[(Benzyloxy)methyl]oxetan-3-yl}methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 44C, 1.37 mg, 3.56 mmol) was hydrogenated using the procedure from Compound 38A to afford 998 mg of the title compound (95%). 1H NMR (400 MHz, CD3OD) δ 7.86 (s, 1H), 7.67 (s, 1H), 4.65 (d, J=6.3 Hz, 2H), 4.49 (s, 2H), 4.42 (d, J=6.3 Hz, 2H), 3.57 (s, 2H), 1.32 (s, 12H).

Sources & evidence

ORD record
ord-f3310b915e704d40970b60439819b117
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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