Cyclopropanemethanamine → 4-Chloro-6-(cyclopropylmethyl-amino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 2252868Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[NH2:13][CH2:14][CH:15]1[CH2:17][CH2:16]1>>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

Reactant 2

HCID 75646Cyclopropanemethanamine

HCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 99650244-Chloro-6-(cyclopropylmethyl-amino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Procedure

Prepared as described above in Example 2 starting from 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde and (aminomethyl)cyclopropane to give the title compound 4-chloro-6-(cyclopropylmethyl-amino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 0.32 (m, 2H), 0.59 (m, 2H), 1.12 (m, 1H), 2.55 (s, 3H), 3.46 (m, 2H), 9.35 (br s, 1H), 10.28 (s, 1H). LC MS (m/e)=258 (MH+).

Workup

customPrepared

Sources & evidence

ORD record: ord-41f5f7dcf33d4e98b03187857c7ca37b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323472B2

Reaction notes

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