Sodium Bicarbonate → HCID 46897521, compound

HRID 220064Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:11][CH2:10]2)[C:3]=1[NH2:12].[CH2:13]([C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18])[CH3:14].C([O-])(O)=O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:12][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[N:23][C:15]=2[CH2:13][CH3:14])=[C:4]([NH:8][CH:9]2[CH2:10][CH2:11]2)[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-Chloro-N-cyclopropylpyrimidine-4,5-diamine (cf. Journal of Combinatorial Chemistry (2003), 5(5), 653-659) (3.0 g, 16.2 mmol) was initially charged in a mixture of methylene chloride (12.20 ml) and pyridine (3.94 ml). The suspension was cooled to 0° C., and solid 2-ethylnicotinoyl chloride (1.2 eq) was added. The reaction mixture was allowed to warm to room temperature and stirred until the reaction had gone to completion. 10 ml of methylene chloride were then added, the suspension turning into a solution. About 10 ml of semisaturated NaHCO3 solution were added to the organic phase whilst the mixture was stirred vigorously in a flask using a magnetic stirrer; poorly soluble crystals (product) precipitated and were filtered off with suction, washed 3× with a little water and 3× with n-heptane and dried.

Workup

temperatureto warm to room temperature
stirringwas stirred vigorously in a flask
custompoorly soluble crystals (product) precipitated
filtrationwere filtered off with suction
washwashed 3× with a little water and 3× with n-heptane
customdried

Sources & evidence

ORD record: ord-194775e49e8c430284b6739eb899edaf
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202877B2

Reaction notes

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