1-Methylpiperazine → 4-{[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-4-phenyl-1h-imidazol-1-yl]methyl}cyclohexanol

HRID 32630Notes

Reaction equation

HRID 32630 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[N:15]([CH2:16][CH:17]4[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]4)[CH:14]=[N:13][C:12]=3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CN1CCNCC1>CC#N>[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[N:15]([CH2:16][CH:17]4[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]4)[CH:14]=[N:13][C:12]=3[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 100012704-{[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-4-phenyl-1H-imidazol-1-yl]methyl}cyclohexanone

Product 1

HCID 104764434-{[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-4-phenyl-1h-imidazol-1-yl]methyl}cyclohexanolYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-{[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-4-phenyl-1H-imidazol-1-yl]methyl}cyclohexanone (Example 179), (100 mg) was treated with sodium triacetoxyborohydride (160 mg) and 1-methylpiperazine (150 mg) in MeCN (20 mL) for 4 days at ambient temperature. The mixture was filtered and the solids washed with MeCN (2×5 mL). The combined filtrate and washes were evaporated and the residue was purified by preparative RPHPLC (eluting with a gradient of water and MeCN containing 0.1% TFA) to afford the title alcohol as a colourless solid (15 mg, 16%);

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids washed with MeCN (2×5 mL)
  3. customThe combined filtrate and washes were evaporated
  4. customthe residue was purified by preparative RPHPLC (
  5. washeluting with a gradient of water and MeCN containing 0.1% TFA)

Sources & evidence

ORD record
ord-795d48069cd34ada8dff65468d9f44e5
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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