Acetic Acid → 7-{4-[2-(4-methylpiperazino)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 51599Notes

Reaction equation

HRID 51599 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][CH:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([CH2:31][CH2:30][CH:27]2[CH2:28][CH2:29][CH:24]([N:8]3[C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[C:10]([C:11]4[CH:16]=[CH:15][C:14]([O:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:13][CH:12]=4)=[CH:9]3)[CH2:25][CH2:26]2)[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 227361722-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetaldehyde

Product 1

HCID 227362597-{4-[2-(4-methylpiperazino)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 52.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetaldehyde (0.025 g, 0.059 mmol), N-methylpiperazine (0.0083 g, 0.083 mmol) and acetic acid (0.0035 g, 0.059 mmol) in 1,2-dichloroethane (0.4 mL) was stirred for 10 min at ambient temperature and sodium triacetoxyborohydride (0.019 g, 0.089 mmol) was added. The mixture was stirred at ambient temperature under an atmosphere of nitrogen for 6 hours and the solvent removed under reduced to yield a yellow oil. The compound was purified by preparative RP-HPLC to yield 7-{4-[2-(4-methylpiperazino)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.016 g, 0.031 mmol) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.27(s, 1H), 7.45(d, 2H), 7.37(t, 2H), 7.16(t, 1H), 7.09(m, 5H), 5.57(br, 2H), 4.73(m, 1H), 2.33(s, 3H), 2.49-1.65(m, 19H); RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% acetonitrile-0.05M ammonium acetate over 10 min, 1 mL/min) Rt 8.15 min. MS: MH+ 511.

Workup

  1. stirringThe mixture was stirred at ambient temperature under an atmosphere of nitrogen for 6 hours
  2. customthe solvent removed
  3. customto yield a yellow oil
  4. customThe compound was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-0f775cb481224b3da334d787c3e9fefe
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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