4-Amino-2-methyl-5-pyrimidinemethanamine → 4-{6-[(4-Amino-pyrimidin-5-ylmethyl)-amino]-5-bromo-pyridine-3-sulfonyl}-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

HRID 2216077

Reaction equation

HRID 2216077 reaction equation
C(OC(=O)[NH:7][C:8]([C:10]1[S:11][C:12]([S:26][CH3:27])=[C:13]([S:15]([C:18]2[CH:19]=[N:20][C:21](Cl)=[C:22]([Br:24])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])(C)(C)C.[NH2:29][C:30]1[C:35]([CH2:36][NH2:37])=[CH:34][N:33]=[C:32](C)[N:31]=1.C(Cl)Cl.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>C1COCC1>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[NH2:29][C:30]1[C:35]([CH2:36][NH:37][C:21]2[N:20]=[CH:19][C:18]([S:15]([C:13]3[CH:14]=[C:10]([C:8]([NH2:9])=[NH:7])[S:11][C:12]=3[S:26][CH3:27])(=[O:16])=[O:17])=[CH:23][C:22]=2[Br:24])=[CH:34][N:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 667624-Amino-2-methyl-5-pyrimidinemethanamineHCID 21863450Trifluoroacetic acid methylene chlorideHCID 140043501tert-butyl N-[4-[(5-bromo-6-chloro-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 218864504-{6-[(4-Amino-pyrimidin-5-ylmethyl)-amino]-5-bromo-pyridine-3-sulfonyl}-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was conducted following the procedure for Example 164: step c, using {[4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.035 g, 0.067 mmol), 4-amino-5-aminomethyl-2-methylpyrimidine (0.018 g, 0.135 mmol), THF [2 mL], followed by DCM/TFA (1:1) and reverse-phase HPLC to yield the title compound. ESI-MS (m/z): Calcd. for C18H19BrN6O2S3: 528.48 (M+H); found 528.0, 529.9.

Sources & evidence

ORD record
ord-7b4d4ea3689b47a69936d134fa6fc0ff
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Linked notes

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