Sodium triacetoxyborohydride → HCID 58233987, compound

HRID 390936Notes

Reaction equation

HRID 390936 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:34][C:15]3[N:16]=[C:17]([C:26]4[CH:27]=[N:28][CH:29]=[C:30]([CH:33]=4)[CH:31]=[O:32])[N:18]=[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[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+].O.C(Cl)Cl>ClCCCl>[O:23]1[CH2:24][CH2:25][N:20]([C:19]2[C:14]3[CH:13]=[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)[S:34][C:15]=3[N:16]=[C:17]([C:26]3[CH:33]=[C:30]([CH2:31][OH:32])[CH:29]=[N:28][CH:27]=3)[N:18]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 21908982Water methylene chlorideHCID 86623530HCID 86623530, compound

Product 1

HCID 58233987HCID 58233987, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-(6-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[2,3-d]pyrimidin-2-yl)nicotinaldehyde (95 mg) and sodium triacetoxyborohydride (55 mg) in dry 1,2-dichloroethane (10 mL) was heated at 40° C. overnight. A further portion of sodium triacetoxyborohydride (49 mg) was then added and heating continued for another 4 h. Water/CH2Cl2 work up then purification on silica yielded 232 (37 mg). NMR (CDCl3): 2.65-2.67 (m, 4H, 2×CH2), 2.80 (s, 3H, CH3), 3.27-3.30 (m, 4H, 2×CH2), 3.82 (s, 2H, CH2), 3.88-3.91 (m, 4H, 2×CH2), 3.97-4.0 (m, 4H, 2×CH2), 4.84 (s, 2H, CH2), 7.17 (s, H, ArH), 8.67 (s, H, ArH), 8.69 (s, H, ArH), 9.55 (s, H, ArH). MS: (ESI+): MH+ 505.18

Workup

  1. temperatureheating
  2. custompurification on silica

Sources & evidence

ORD record
ord-ff0b602093c245839b7c9e4515b2d674
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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