Ammonium Chloride → HCID 86691222, compound

HRID 1887059Notes

Reaction equation

[CH2:1]([N:8]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:18][CH:17]=2)[C:10]=1[N+:31]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>C1COCC1.CO.O.[Fe]>[NH2:31][C:10]1[C:11]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:20][CH:21]=2)=[N:12][CH:13]=[N:14][C:9]=1[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl 4-(6-(dibenzylamino)-5-nitropyrimidin-4-ylamino)phenyl(methyl)carbamate (37) (6 g, 11.1 mmol) in THF/MeOH/H2O (100 mL/100 mL/30 mL) was added Fe powder (3.11 g, 55.5 mmol) and NH4Cl (5.94 g, 111 mmol). The reaction mixture was heated at 60° C. for 4 h under N2. After cooling to rt, the reaction mixture was filtered through a pad of Celite. The filtrate was extracted with EtOAc (100 mL×3), washed with water and brine, dried over Na2SO4, and concentrated in vacuo to afford tert-butyl 4-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenyl(methyl)carbamate (38) (5.4 g, yield 95%) as a yellow solid. LC-MS (ESI): m/z (M+1) 511.

Workup

temperatureAfter cooling to rt
filtrationthe reaction mixture was filtered through a pad of Celite
extractionThe filtrate was extracted with EtOAc (100 mL×3)
washwashed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-391ac6b23a14428e9c18cde39c4c3ec5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501724B1

Reaction notes

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