Diisopropylethylamine → (S)-4-Chloro-2,5-diformamido-6-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxyamino)pyrimidine

HRID 1089276Notes

Reaction equation

Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][CH:13]=[O:14])[N:3]=1.[CH3:15][C:16]1([CH3:24])[O:20][C@H:19]([CH2:21][O:22][NH2:23])[CH2:18][O:17]1.C(N(C(C)C)CC)(C)C>COCCOCCOC>[Cl:11][C:6]1[C:7]([NH:8][CH:9]=[O:10])=[C:2]([NH:23][O:22][CH2:21][C@@H:19]2[CH2:18][O:17][C:16]([CH3:24])([CH3:15])[O:20]2)[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (7.3 g, 31.1 mmol), (S)-2,2-dimethyl-1,3-dioxolan-4-ylmethoxyamine (4.6 g, 31.1 mmol) and diisopropylethylamine (8.03 g, 62.1 mmol) in diglyme (125 ml) was stirred at 100° C. for 4 h. The reaction was filtered, evaporated and the residue chromatographed twice in chloroform-methanol 15:1 affording (S)-4-chloro-2,5-diformamido-6-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxyamino)pyrimidine(2.6 g, 24%). υmax (CHCl3) 3400, 1700, 1580, 1560 and 1470 cm-1 ; δH (CDCl3) 1.39(3H,S,CH3), 1.48(3H,S,CH3) , 3.60-4.65(5H,m,CH2ONH+CH2OCMe2 +CHOCMe2), 7.96(1H,br.m, D2O exchangeable, NH), 8.34(1H,S,CHO), 9.25(2H,br.m,D2O exchangeable, 2XNH) and 9.50(1H,S,CHO); m/z 344(M+ -H,<1%), 330(M+ -CH3, <1%).

Workup

filtrationThe reaction was filtered
customevaporated
customthe residue chromatographed twice in chloroform-methanol 15:1 affording (S)-4-chloro-2,5-diformamido-6-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxyamino)pyrimidine(2.6 g, 24%)

Sources & evidence

ORD record: ord-6f2fd3abb9f84eb2b19c35147ec7d202
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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