Ammonium Hydroxide → 4-(2-[1,3]Dioxan-2-yl-ethyl)-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-2-ylamine

HRID 2196121Notes

Reaction equation

HRID 2196121 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH2:19][CH2:20][CH:21]2[O:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[OH-].[NH4+:28]>CC(O)C>[O:22]1[CH2:23][CH2:24][CH2:25][O:26][CH:21]1[CH2:20][CH2:19][C:4]1[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=[C:2]([NH2:28])[N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 579067552-Chloro-4-(2-[1,3]dioxan-2-yl-ethyl)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine

Product 1

HCID 249638714-(2-[1,3]Dioxan-2-yl-ethyl)-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-2-ylamineYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-chloro-4-(2-[1,3]dioxan-2-yl-ethyl)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (9 mg, 0.024 mmol) in iPrOH (0.5 mL) and 30% ammonium hydroxide (4 mL) was heated at 100° C. for 30 minutes. Solvents were concentrated in vacuo and the residue was purified by RP HPLC using a C18 column with a gradient of H2O and 0.1% TFA-acetonitrile, to provide the title compound as a white solid (6 mg, yield: 70%). The resulting title compound was characterised as follows: MS (m/z) 355.0 [M+H]+; HPLC Rt=3.34 minutes (Method A).

Workup

  1. concentrationSolvents were concentrated in vacuo
  2. customthe residue was purified by RP HPLC

Sources & evidence

ORD record
ord-20dcae2338094412b02ba0cc157de25e
Source dataset
uspto-grants-2012_12
Patent number
US08338435B2

Reaction notes

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