2-Pyridinemethanamine → 5-phenyl-N-(pyridin-2-ylmethyl)-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4-amine

HRID 2036852Notes

Reaction equation

HRID 2036852 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9](=O)[NH:10][C:11]([C:17]2([CH3:25])[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19][CH2:18]2)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:27]1[CH2:37][CH2:36][N:35]2[C:30](=[N:31]CCC2)[CH2:29][CH2:28]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.NCC1C=CC=CN=1>CC#N>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:35][CH2:36][C:37]2[CH:27]=[CH:28][CH:29]=[CH:30][N:31]=2)=[N:10][C:11]([C:17]2([CH3:25])[CH2:18][O:19][C:20]([CH3:24])([CH3:23])[O:21][CH2:22]2)=[N:12]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 195092-PyridinemethanamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 136392063HCID 136392063, compound

Product 1

HCID 510303655-phenyl-N-(pyridin-2-ylmethyl)-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4-amineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-phenyl-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4(3H)-one (0.22 g, 0.62 mmol) in MeCN (10 mL) at room temperature was added DBU (0.24 g, 1.57 mmol) and BOP reagent (0.36 g, 0.81 mmol). Upon completion of addition, the reaction mixture was stirred for 30 min. Aminomethylpyridine (0.11 ml, 1.13 mmol) was added and the resulting mixture was stirred for an additional 16 h. After this time, the reaction mixture was concentrated and purified by silica gel column chromatography (2% MeOH in DCM) to provide 5-phenyl-N-(pyridin-2-ylmethyl)-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4-amine (0.18 g, 68% yield) as a white solid. LCMS Method V: retention time 2.21 min, [M+1]=531.2.

Workup

  1. additionUpon completion of addition
  2. stirringthe resulting mixture was stirred for an additional 16 h
  3. concentrationAfter this time, the reaction mixture was concentrated
  4. custompurified by silica gel column chromatography (2% MeOH in DCM)

Sources & evidence

ORD record
ord-3d7ff2b27ff54142bf90f72f5940a7f7
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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