Ammonia → 6-(4-Aminobenzyl)pyrimidin-4-amine

HRID 1993591Notes

Reaction equation

HRID 1993591 reaction equation
Cl.O1CCOCC1.C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:27]=[C:26]([NH2:28])[N:25]=[CH:24][N:23]=2)=[CH:17][CH:16]=1)(C)(C)C.N>C(Cl)Cl>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[N:23]=[CH:24][N:25]=[C:26]([NH2:28])[CH:27]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58659458[4-(6-Amino-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 586593986-(4-Aminobenzyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4 N solution of HCl in dioxane (19.2 mL, 76.4 mmol, 30 equiv) is added to a solution of [4-(6-amino-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (770 mg, 2.56 mmol) in CH2Cl2 (23 mL), under an argon atmosphere. The resulting white suspension is stirred at rt for 1.5 h and concentrated in vacuo. To the residue is added a 2 M methanolic solution of ammonia (3.8 mL, 7.68 mmol, 3 equiv) and the resulting yellow solution is concentrated in vacuo. The crude product is purified by silica gel (90 g) column chromatography CH2Cl2/MeOH, 90/10, then 80/20). The title compound is obtained as a white solid: ES-MS: 201.0 [M+H]+; single peak at tR=2.00 min (System 2); Rf=0.20 (CH2Cl2/MeOH, 90/10).

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationthe resulting yellow solution is concentrated in vacuo
  3. customThe crude product is purified by silica gel (90 g) column chromatography CH2Cl2/MeOH, 90/10

Sources & evidence

ORD record
ord-d6922905512e4ee09df647ee9583d0f0
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…