2-Aminopyrimidine → HCID 90717450, compound

HRID 1993498Notes

Reaction equation

CS(O[C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH2:9]3)[CH2:7]1)[CH2:13]2)(=O)=O.[NH2:24][C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1>>[C:20]([O:19][C:17](=[O:18])[NH:16][C:8]12[CH2:14][CH:12]3[CH2:11][CH:10]([CH2:15][C:6]([NH:24][C:25]4[N:30]=[CH:29][CH:28]=[CH:27][N:26]=4)([CH2:13]3)[CH2:7]1)[CH2:9]2)([CH3:23])([CH3:22])[CH3:21]

Participants

Reactant 2

HCID 79782-Aminopyrimidine

HCID 59134554HCID 59134554, compound

Product 1

HCID 90717450HCID 90717450, compound

Procedure

The mixture of 1.04 g (3 mmole) of 3-[(tert-butoxycarbonyl)amino]-1-adamantyl methanesulphonate and 1.0 g (10.5 mmole) 2-aminopyrimidine are melted at 140° C. After 15 minutes of stirring the melt is cooled down and purified by column chromatography (n-hexane—ethyl acetate—chloroform 2:1: 1). The product is white crystalline material, 0.7 g (68%). Mp.: 163-165° C. 1H-NMR (DMSO-d6): 1.36 (s, 9H), 1.52 (s, 2H), 1.71 (d, 2H), 1.86 (d, 4H), 2.07 (m, 4H), 2.25 (m, 2H), 6.38 (s, 1H), 6.49 (t, 3H), 6.58 (s, 1H), 8.22 (d, 2H).

Workup

temperatureis cooled down
custompurified by column chromatography (n-hexane—ethyl acetate—chloroform 2:1: 1)

Sources & evidence

ORD record: ord-49d81498a68e49a49af1ba433ad6f74e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652021B2

Reaction notes

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