Sodium triacetoxyborohydride → HCID 58233972, compound

HRID 1365258Notes

Reaction equation

[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:20][C:19]3[C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:17][C:16]([C:27]4[CH:28]=[C:29]([CH:33]=[O:34])[CH:30]=[N:31][CH:32]=4)=[N:15][C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[O:24]1[CH2:23][CH2:22][N:21]([C:18]2[C:19]3[S:20][C:12]([CH2:11][N:8]4[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH2:9]4)=[CH:13][C:14]=3[N:15]=[C:16]([C:27]3[CH:28]=[C:29]([CH2:33][OH:34])[CH:30]=[N:31][CH:32]=3)[N:17]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 40 °C

Procedure

To 60 mg of 5-[6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-pyridine-3-carbaldehyde 241 (Example 158) in dry DMF was added sodium triacetoxyborohydride (66 mg) and the reaction mixture was heated at 40° C. overnight. After the SCX-2 cartridge work-up, purification on silica and recrystallization from DCM/hexane gave 235 (45 mg). NMR (CDCl3): 1.80-1.90 (1H, br, OH), 2.67-2.71 (4H, m), 2.81 (3H, s), 3.29-3.33 (4H, m), 3.89 (2H, s), 3.89-3.93 (4H, m), 4.08-4.12 (4H, m), 4.86 (2H, s), 7.35 (1H, s), 8.70 (1H, s), 8.71 (1H, s), 9.56 (1H, s). MS (ESI+): MH+505.17 (100%)

Workup

customAfter the SCX-2 cartridge work-up, purification
customon silica and recrystallization from DCM/hexane

Sources & evidence

ORD record: ord-db39be234e974e3d912e80f08bb9b23b
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888352B2

Reaction notes

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