Methanol → 6-[(N-phenylanilino)methyl]pteridine-2,4-diamine

HRID 1827692Notes

Reaction equation

HRID 1827692 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.[NH2:17][C:18]1[N:27]=[C:26]([NH2:28])[C:25]2[C:20](=[N:21][CH:22]=[C:23]([CH2:29]Br)[N:24]=2)[N:19]=1.CO>C1COCC1>[NH2:17][C:18]1[N:27]=[C:26]([NH2:28])[C:25]2[C:20](=[N:21][CH:22]=[C:23]([CH2:29][N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:24]=2)[N:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11487DiphenylamineHCID 24758Sodium hydride2×HCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Product 1

HCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Powdered NaH (50 mg, 2.1 mmol) is added to a stirred solution of diphenylamine (1.3 g, 0.77 mmol) in dry THF (10 mL) at 0° C. under N2. After 10 min, 2,4-diamino-6-bromomethylpteridine hydrobromide (100 mg, 0.3 mmol) is added and the reaction mixture is allowed to come to room temperature and left to stir for 2 days. The excess NaH is decomposed with MeOH (1 mL) and the mixture is concentrated to dryness by rotary evaporation. Flash chromatography on silica gel with 95:5 CHCl3-MeOH as the eluent affords the product, N-(2,4-diaminopteridin-6-yl)methyl-N,N-diphenylamine, as a bright-yellow powder (56 mg, 54% yield); mp >250° C. dec.; MS (FAB) m/z (M+1)=344; IR (KBr) v 3450, 3340, 3170, 1630, 1590, 1550, 1490, 1450, 1360, 1220 cm−1; 1H NMR(d6-DMSO) δ 5.10 (s, 2H, CH2), 6.70 (m, 10H, aromatic), 8.60 (s, 1H, C7-H. Anal. Calcd for C19H17N7.0.8H2O: C, 63.73; H, 5.23; N, 27.40. Found: C, 64.15; H, 4.85; N, 27.07.

Workup

  1. customto come to room temperature
  2. waitleft
  3. concentrationthe mixture is concentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-f4fe756946d141219f80a890b9739371
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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