Benzylamine → HCID 70005645, compound

HRID 1355848Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[N:4][C:5]([NH2:11])=[N:6][C:7]=1S(C)=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1>[CH2:17]([NH:24][C:7]1[C:2]([Br:1])=[C:3]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[N:4]=[C:5]([NH2:11])[N:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred suspension of 200 mg (0.66 mmol) 5-bromo-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine in 5 ml dioxane was added 0.16 ml (1.46 mmol) benzylamine and the mixture heated at 100° C. for 2 hour. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether/hexane afforded 162 mg (71%) N4-benzyl-5-bromo-6-furan-2-yl-pyrimidine-2,4-diamine as a white crystalline solid. EI-MS m/e (%): 346 (M{81Br}+, 50), 344 (M{79Br} +51), 265 (46), 106 (100), 91 (61).

Workup

concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-2804da5c79284219bf5dc3ea181ee8e6
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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