Sodium Nitrite → HCID 86655317, compound

HRID 2096667Notes

Reaction equation

HRID 2096667 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C@H:19]3[CH2:23][CH2:22][O:21][CH2:20]3)[N:12]=2)[C:3]=1[NH2:24].[N:25]([O-])=O.[Na+]>CCO.C(O)(=O)C.O>[Cl:1][C:2]1[C:3]2[N:24]=[N:25][N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C@H:19]4[CH2:23][CH2:22][O:21][CH2:20]4)[N:12]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

6

Reactant 2

HCID 23668193Sodium NitriteHCID 86655316HCID 86655316, compound

Product 1

HCID 86655317HCID 86655317, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-chloro-N4-{6-[(S)-(tetrahydrofuran-3-yl)oxymethyl]pyridin-2-ylmethyl}pyrimidine-2,4,5-triamine (8.09 g, 23.06 mmol) in EtOH (85 mL) and glacial acetic acid (21 mL) at 0° C., was treated with a solution of sodium nitrite (2.07 g, 29.979 mmol) in water (5.3 mL), stirred at 0° C. for 1 h and the resulting precipitate was filtered, washed with EtOH (85 mL) and dried to give the title compound (5.82 g, 70%) as an off-white solid; LC-MS retention time 1.94 min, (M+H)+ 362.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with EtOH (85 mL)
  3. customdried

Sources & evidence

ORD record
ord-c47fda04f39245729359fd1892ce1357
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

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