Water → HCID 90314282, compound

HRID 1523897Notes

Reaction equation

HRID 1523897 reaction equation
[NH2:1][C:2]1[C:3]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=3)=[C:17]([F:28])[CH:16]=2)=[N:4][CH:5]=[N:6][CH:7]=1.[OH2:29].CC#N.C(Cl)[Cl:34].[OH2:36]>>[ClH:34].[NH2:1][C:2]1[C:3]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[N:25][C:24]([NH2:27])=[N:23][CH:22]=3)=[C:17]([F:28])[CH:16]=2)(=[O:36])=[O:29])=[N:4][CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 21961003HCID 21961003, compoundHCID 90313163HCID 90313163, compound

Product 1

HCID 90314282HCID 90314282, compound

Procedure

To a solution of 5-{2′-[(5-aminopyrimidin-4-yl)sulfanyl]-3-fluorobiphenyl-4-yl}-pyrimidin-2-amine (200 mg, 0.51 mmol) in MeCN/DCM/H2O (5 mL/5 mL/5 mL) were added NaIO4 (326 mg, 1.50 mmol) and RuCl3 (16 mg, 0.075 mmol). The reaction mixture was stirred at rt for 10 hours then poured into water (50 mL) and extracted with EtOAc (30 mL×3). The combined organic extracts were concentrated and purified by HPLC to give the title compound as a white solid. MS (ESI): mass calcd. for C20H15FN6O2S, 422.10; m/z found, 423.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.57 (s, 2H), 8.30-8.25 (m, 2H), 8.22 (s, 1H), 7.83 (m, 1H), 7.77 (m, 1H), 7.44-7.33 (m, 2H), 6.88 (d, J=9.5, 2H), 6.29 (s, 2H).

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. concentrationThe combined organic extracts were concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-2b1d0eff80f24ddc98cd81ed01be6c7d
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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