Methylamine → HCID 67297986, compound

HRID 1520373Notes

Reaction equation

HRID 1520373 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[N:16][CH:15]=[CH:14][N:13]=1)[NH:6][C:5]2=O.F[P-](F)(F)(F)(F)F.[N:26]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2C=CC=CC=2N=N1.N12CCCN=C1CCCCC2.CN.C1COCC1>O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[N:16][CH:15]=[CH:14][N:13]=1)[N:6]=[C:5]2[NH:26][CH3:30]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 136334004HCID 136334004, compound

Product 1

HCID 67297986HCID 67297986, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100 mL round-bottomed flask was added 6-iodo-2-(pyrazin-2-yl)quinazolin-4(3H)-one (0.500 g, 1.428 mmol), BOP (0.821 g, 1.857 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.426 ml, 2.86 mmol) in DMT (10 mL) to give a colorless solution. Methylamine, 2M in THF (2.142 ml, 4.28 mmol) was added and stirred at room temperature overnight. The reaction mixture was diluted with water (50 mL) and then a precipitate formed. The resulting solid was collected by filtration and dried to give 0.515 g of 6-iodo-N-methyl-2-(pyrazin-2-yl)quinazolin-4-amine as a pale brown solid in a 99% yield. LCMS m/z=364 (M+1) (Method D) (retention time=1.25 min). 1H NMR (300 MHz, DMSO) δ 9.60 (s, 1H), 8.89-8.65 (m, 3H), 8.65-8.48 (m, 1H), 8.06 (d, J=8.7 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 3.11 (d, J=4.2 Hz, 3H).

Workup

  1. customto give a colorless solution
  2. customa precipitate formed
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-1d414ec489e04e469de588c96b236b96
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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