Ammonia → HCID 44409937, compound

HRID 1984316Notes

Reaction equation

HRID 1984316 reaction equation
[N:1]1([C:8]2[N:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]=[C:10]([NH:17][CH:18]3[CH2:20][CH2:19]3)[C:9]=2[N+:21]([O-])=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].N>O1CCOCC1.O.C(OCC)(=O)C>[N:1]1([C:8]2[N:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]=[C:10]([NH:17][CH:18]3[CH2:19][CH2:20]3)[C:9]=2[NH2:21])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 44409787HCID 44409787, compound

Product 1

HCID 44409937HCID 44409937, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-(1-azepanyl)-N,2-dicyclopropyl-5-nitro-4-pyrimidinamine 197 (0.5 g, 16 mmol) in 1,4-dioxane (35 ml) and water (35 ml) is added sodium hydrosulfite (2.19 g, 13 mmol) and ammonia (25% solution, 1.2 ml). The mixture is stirred at room temperature for 10 h then diluted with ethyl acetate and washed three times with water. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo to afford a yellow oil. The crude oil is purified by column chromatography (dichloromethane/ethanol/ammonia: 95/5/0.5) to give pure 6-(1-azepanyl)-N4,2-dicyclopropyl-4,5-pyrimidinediamine 63 (137 mg, 30%) as a reddish solid.

Workup

  1. washwashed three times with water
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford a yellow oil
  5. customThe crude oil is purified by column chromatography (dichloromethane/ethanol/ammonia: 95/5/0.5)

Sources & evidence

ORD record
ord-3c456d309596444ebd0d37ae13530fb9
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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