Methylamine → N-cyano-N'-methyl-N"-[2-(2-pyrimidylmethylthio)ethyl]guanidine

HRID 2398352Notes

Reaction equation

ClC[C:3]1[N:8]=[CH:7]C=[CH:5][N:4]=1.C1(=O)[N:13](C(S)C)C(=O)C2=CC=CC=C12.[NH2:23][CH2:24][CH2:25][S:26][CH2:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.CN>>[C:5]([NH:4][C:3]([NH:8][CH3:7])=[N:23][CH2:24][CH2:25][S:26][CH2:27][C:28]1[N:29]=[CH:30][CH:31]=[CH:32][N:33]=1)#[N:13]

Participants

Reactant 4

HCID 6329Methylamine

HCID 128773712-(Chloromethyl)pyrimidine

HCID 202424852-[(2-Aminoethyl)thiomethyl]pyrimidine

HCID 214047132-(1-Sulfanylethyl)isoindole-1,3-dione

Product 1

HCID 178484995N-cyano-N'-methyl-N"-[2-(2-pyrimidylmethylthio)ethyl]guanidine

Procedure

Reacting 2-chloromethylpyrimidine with phthalimidoethanethiol by the procedure of Example 1(i)(b) and then reacting the resulting 2-[(2-aminoethyl)thiomethyl]pyrimidine with dimethyl-N-cyanoimidodithiocarbonate and methylamine by the procedure of Example 3(d) gives N-cyano-N'-methyl-N"-[2-(2-pyrimidylmethylthio)ethyl]guanidine.

Sources & evidence

ORD record: ord-db623a3429fa4de0947a56d9aff2039b
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04024271

Reaction notes

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