N-Iodosuccinimide → N4-(Cyclopropylmethyl)-5-iodopyrimidine-2,4-diamine

HRID 79146

Reaction equation

[I:1]N1C(=O)CCC1=O.[CH:9]1([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[CH2:11][CH2:10]1>CC(O)=O>[CH:9]1([CH2:12][NH:13][C:14]2[C:19]([I:1])=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

N-iodosuccinimide (11.5 g, 50.9 mmol) was added to a solution of compound 237 (7.60 g, 46.3 mmol) in AcOH (90 mL). The reaction was warmed to 80° C. and stirred for 1.5 h. Solvent was removed in vacuo. The residue was taken up in dichloromethane (200 mL) and water. The aqueous layer was brought to pH 12 with 5 N NaOH and organics were sequestered. The aqueous was extracted further with dichloromethane (2×100 mL). The combined organics were treated with solid sodium thiosulfate, dried with MgSO4 and concentrated in vacuo. Silica gel chromatography (gradient elution 10 to 75% ethyl acetate in hexanes) afforded compound 238 (8.0 g, 60% yield).

Workup

customSolvent was removed in vacuo
extractionThe aqueous was extracted further with dichloromethane (2×100 mL)
additionThe combined organics were treated with solid sodium thiosulfate
dry with materialdried with MgSO4
concentrationconcentrated in vacuo
washSilica gel chromatography (gradient elution 10 to 75% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-bf5e72b479724e449a607398db936fdd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841312B2

Linked notes

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