Methanol → HCID 486241, compound

HRID 1827693Notes

Reaction equation

HRID 1827693 reaction equation
[H-].[Na+].[CH:3]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Br.[NH2:18][C:19]1[N:28]=[C:27]([NH2:29])[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH2:30]Br)[N:25]=2)[N:20]=1.CO>C1COCC1>[NH2:18][C:19]1[N:28]=[C:27]([NH2:29])[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH2:30][N:15]3[C:16]4[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=4[O:8][C:9]4[C:14]3=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydride2×HCID 67278PhenoxazineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Product 1

HCID 486241HCID 486241, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60% oil suspension containing 51 mg, 2.0 mmol) was added to a stirred solution of phenoxazine (147 mg, 0.784 mmol) in dry THF (10 mL) at 0° C. under N2. After 10 min. 2,4-diamino-6-bromomethylpteridine hydrobromide (100 mg, 0.392 mmol) was added and the reaction mixture was allowed to come to room temperature and left to stir for 2 days. The excess NaH was decomposed with MeOH (1 mL), and the mixture was concentrated to dryness by rotary evaporation. Flash chromatography on silica gel yielded the title compound, N-[(2,4-diaminopteridin-6-yl)methyl]phenoxazine, as a brown solid; yield 47 mg (34%); mp >250° C. dec. Anal. Calcd. for C19H15N7O0.4H2O: C, 62.60; H, 4.37. Found: C, 62.84; H, 4.10.

Workup

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

Sources & evidence

ORD record
ord-b628f74a68624ca08b46c92469beeb03
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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