Citric Acid → HCID 178456867, compound

HRID 2421008Notes

Reaction equation

[C:1]([C:3]1[C:4]([NH:18][CH2:19][CH2:20][CH3:21])=[N:5][C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:7][CH:8]=1)#[N:2].[Cl-].[NH4+].[N-:24]=[N+:25]=[N-:26].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)(Cl)Cl.CN(C=O)C>[CH2:19]([NH:18][C:4]1[C:3]([C:1]2[NH:26][N:25]=[N:24][N:2]=2)=[CH:8][N:7]=[C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[N:5]=1)[CH2:20][CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To 20 mL of DMF, the total amount of 5-cyano-4-n-propylamino-2-[2-(4-pyridyl)ethylamino]pyrimidine obtained in Step 2 was dissolved, then DMF (16 mL) solution of ammonium chloride (856 mg) and sodium azide (1.04 g) was added thereto, followed by stirring at 100° C. for 24 hours. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was added with chloroform and 5% an aqueous citric acid solution, and then the mixture was separated. The pH of an aqueous layer was adjusted to about 6 and the crystals were precipitated. The crystals were collected by filtration, washed with water, then dried fully under reduced pressure to give 4-n-propylamino-2-[2-(4-pyridyl)ethylamino]-5-tetrazolylpyrimidine [Compound (Z) in which R1 is n-propylamino and R2 is 2-(4-pyridyl)ethylamino] (700 mg, overall yield from 4-chloro-5-cyano-2-methylthiopyrimidine: 22%).

Workup

customthe mixture was separated
customthe crystals were precipitated
filtrationThe crystals were collected by filtration
washwashed with water
customdried fully under reduced pressure

Sources & evidence

ORD record: ord-e77ba93eed114f16b88f6604540b9f86
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956060B2

Reaction notes

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