Bicarbonate Ion → Ammonium Hydroxide

HRID 1876206Notes

Reaction equation

HRID 1876206 reaction equation
Cl.Cl[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C([N:25](C(C)C)C(C)C)C.[CH3:32][NH:33][CH2:34][CH2:35][CH2:36][NH2:37].C(=O)(O)[O-:39]>C(O)CCC.C(Cl)(Cl)Cl>[NH2:37][CH2:36][CH2:35][CH2:34][N:33]([CH3:32])[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[NH4+:25].[OH-:39]

Participants

8

Reactant 4

HCID 769Bicarbonate IonHCID 80511N-Methyl-1,3-propanediamineHCID 81531DiisopropylethylamineHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

Product 2

HCID 14923Ammonium HydroxideHCID 59242013N2-(3-Amino-propyl)-N4-(4-methoxy-phenyl)-N2,N4-dimethyl-quinazoline-2,4-diamine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride (203 mg, 0.604 mmol), ethyl-diisopropyl-amine (0.25 mL, 1.4 mmol) and N1-methyl-propane-1,3-diamine (95%; 100 μL) in n-butanol (4 mL) was heated at 115° C. After 32 h, the rxn was treated with bicarbonate resin (Novabiochem 01-64-0419) then concd. The material was dissolved in CHCl3, adsorbed onto diatomaceous earth and partially purified on an amine column (Isco 68-2203-101) eluting with a gradient of 0-100% i-PrOH in CHCl3. Pure title compound was obtained as a pale yellow oil (23 mg; 11%) after preparative TLC (SiO2/100:20:2 CHCl3:MeOH:concd NH4OH). 1H NMR (DMSO-d6) δ 7.38-7.27 (m, 2H), 7.16 (m, 2H), 6.97 (m, 2H), 6.79 (d, J=8.4 Hz, 1H), 6.65 (m, 1H), 3.77 (s, 3H), 3.76 (m, 2H), 3.44 (s, 3H), 3.17 (s, 3H), 2.63 (t, J=6.6 Hz, 2H), 1.75 (m, 2H); LC-MS (ESI+; 352 ([M+H]+)).

Workup

  1. custompartially purified on an amine column (Isco 68-2203-101)
  2. washeluting with a gradient of 0-100% i-PrOH in CHCl3

Sources & evidence

ORD record
ord-d714858c2f994b239f5d0542fb54612f
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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