1,2-Dimethoxyethane → 4-(7-Benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-pyrimidin-2-ol

HRID 1678253Notes

Reaction equation

HRID 1678253 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[S:12]1[C:16]([C:17]2[CH:18]=[C:19]([NH2:26])[CH:20]=[C:21]3[C:25]=2[NH:24][N:23]=[CH:22]3)=[CH:15][C:14]2[CH:27]=[CH:28][CH:29]=[CH:30][C:13]1=2.C(N(CC)CC)C.C[O:39]CCOC>>[S:12]1[C:16]([C:17]2[CH:18]=[C:19]([NH:26][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([OH:39])[N:3]=3)[CH:20]=[C:21]3[C:25]=2[NH:24][N:23]=[CH:22]3)=[CH:15][C:14]2[CH:27]=[CH:28][CH:29]=[CH:30][C:13]1=2

Participants

5

Reactant 4

HCID 80711,2-Dimethoxyethane2×HCID 8471TriethylamineHCID 111482324-Chloro-2-(methylsulfonyl)pyrimidineHCID 59023728HCID 59023728, compound

Product 1

HCID 1785177614-(7-Benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-pyrimidin-2-olYield 0.1%

Procedure

To a mixture of 4-chloro-2-methanesulfonyl-pyrimidine (Preparation #1, 1.35 g, 7.0 mmol) in DME (10 mL) was added a mixture of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 1.03 g, 3.9 mmol) and triethylamine (0.76 mL, 5.4 mmol) in DME (70 mL). After about 16 hours at ambient temperature the mixture was filtered, and the solid was purified by reverse phase preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min) to yield 4-(7-Benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-pyrimidin-2-ol (2 mg, 0.006 mmol, 0.1% yield): LC/MS Rt (Method e) 1.3 min; m/z (M−H)− 358.3.

Workup

  1. additionwas added
  2. filtrationAfter about 16 hours at ambient temperature the mixture was filtered
  3. customthe solid was purified by reverse phase preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min)

Sources & evidence

ORD record
ord-23163a45bd6d45db9f73cbd2a7f6da38
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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