4-Methoxybenzylamine → HCID 86663605, compound

HRID 1520743Notes

Reaction equation

HRID 1520743 reaction equation
F[C:2]1[N:23]=[CH:22][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=3)[C:4]=2[CH:3]=1.[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>CS(C)=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:9]2[C:4]3[CH:3]=[C:2]([NH:31][CH2:30][C:29]4[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=4)[N:23]=[CH:22][C:5]=3[N:6]=[CH:7][N:8]=2)=[CH:12][C:13]=1[C:18]([F:20])([F:19])[F:21]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 66823611HCID 66823611, compound

Product 1

HCID 86663605HCID 86663605, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of compound 163 (14.30 g, 43.87 mmol) in DMSO (90 mL) was treated with slow addition of 4-methoxybenzylamine (57.3 mL, 482.52 mmol) under nitrogen at 70° C. The resultant mixture was stirred at 70 to 75° C. for 48 h, then cooled to room temperature and poured into a beaker of ice-water (1 L) with stirring. The resulted solid was collected by filtration, washed with water and dried in a vacuum oven (45° C.) for 2 h. The crude product was triturated with CH2Cl2 to provide N4-(4-fluoro-3-(trifluoromethyl)phenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine (166) (14.40 g, 74%) as a yellow solid, m.p. 202-204° C. 1H NMR [(CD3)2SO] δ 9.83 (s, 1H), 8.77 (s, 1H), 8.38 (s, 1H), 8.27-8.30 (m, 1H), 8.21-8.24 (m, 1H), 7.55 (t, J=9.7 Hz, 1H), 7.28-7.34 (m, 3H), 7.17 (s, 1H), 6.86-6.90 (m, 2H), 4.50 (d, J=6.3 Hz, 2H), 3.71 (s, 3H). Anal. Calcd for C22H17F4N5O: C, 59.59; H, 3.86; N, 15.79%. found: C, 59.31; H, 4.07; N, 15.46%.

Workup

  1. filtrationThe resulted solid was collected by filtration
  2. washwashed with water
  3. customdried in a vacuum oven (45° C.) for 2 h
  4. customThe crude product was triturated with CH2Cl2

Sources & evidence

ORD record
ord-447f1cc33a054a88837e774a3aa4dae5
Source dataset
uspto-grants-2015_07
Patent number
US09073916B2

Reaction notes

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