Acetic Acid → HCID 67385883, compound

HRID 912171Notes

Reaction equation

HRID 912171 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[CH3:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl-].[NH4+]>ClCCl>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([CH2:38][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:48][CH:47]=2)[C:9]2[N:10]=[CH:11][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:37]=[CH:36][C:33]([CH2:34][N:53]6[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]6)=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:13][N:14]=2)=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 59244394HCID 59244394, compound

Product 1

HCID 67385883HCID 67385883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-benzaldehyde (76 mg, 0.118 mmol) in dichloromethane (2 ml), 1-methylpiperazine (40 μl, 0.354 mmol), sodium triacetoxy borohydride (100 mg, 472 mmol) and acetic acid (12.6 μl, 0.236 mmol) were added, followed by stirring at room temperature for 40 hours. To the reaction mixture, saturated aqueous ammonium chloride solution was added, followed by extraction twice with ethyl acetate (10 ml). The organic layer was washed with brine (10 ml), and dried over sodium sulfate, followed by distilling off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/2M-ammonia methanol=100/1 to 30/1), whereby bis-(4-methoxy-benzyl)-(5-{7-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-pyrimidin-2-yl)-amine was obtained as a brown powder (44 mg, 51%).

Workup

  1. extractionfollowed by extraction twice with ethyl acetate (10 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried over sodium sulfate
  4. distillationby distilling off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/2M-ammonia methanol=100/1 to 30/1)

Sources & evidence

ORD record
ord-51c19c1e70594e6a968e10a17f8da791
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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