Sodium triacetoxyborohydride → 2-Chloro-6-(2,2-dimethyl-4-oxetan-3-ylpiperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 1922787Notes

Reaction equation

HRID 1922787 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[CH3:19][C:20]1([CH3:30])[NH:25][CH2:24][CH2:23][N:22]([CH:26]2[CH2:29][O:28][CH2:27]2)[CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][N:25]3[CH2:24][CH2:23][N:22]([CH:26]4[CH2:29][O:28][CH2:27]4)[CH2:21][C:20]3([CH3:30])[CH3:19])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeHCID 674922623,3-Dimethyl-1-(oxetan-3-yl)piperazine

Product 1

HCID 575067452-Chloro-6-(2,2-dimethyl-4-oxetan-3-ylpiperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidineYield 49%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbaldehyde (400 mg, 1.42 mmol), 3,3-dimethyl-1-oxetan-3-ylpiperazine (290 mg, 1.71 mmol) and 4 Å powdered molecular sieves (500 mg) in DCE (20 mL) were allowed to stir at r.t. 3 h before the addition of sodium triacetoxyborohydride (420 mg, 1.98 mmol). The resulting mixture was allowed to stir for 18 h then filtered through Celite®. The filtrate was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%) affording the title compound as a cream solid (305 mg, 49%)._LCMS (method H): RT 2.12 min, [M+H]+ 438.3

Workup

  1. stirringto stir for 18 h
  2. filtrationthen filtered through Celite®
  3. washwas washed with MeOH
  4. washthe product eluted with 2M NH3/MeOH
  5. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%)

Sources & evidence

ORD record
ord-26f3bad393f340ae9b57726e6ba2885d
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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