6-chloro-N4-cyclopropylpyrimidine-4,5-diamine → HCID 86711710, compound

HRID 528021Notes

Reaction equation

HRID 528021 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([O:12][CH3:13])[C:8](=[O:14])[N:7]([CH3:15])[C:6]=2[N:5]=[CH:4][N:3]=1.Cl[C:17]1N=CN=C(NC2CC2)[C:18]=1N>C(#N)C>[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([O:12][CH3:13])[C:8](=[O:14])[N:7]([CH:15]3[CH2:18][CH2:17]3)[C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 105117206-chloro-N4-cyclopropylpyrimidine-4,5-diamineHCID 86711708HCID 86711708, compound

Product 1

HCID 86711710HCID 86711710, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-chloro-8-cyclopropyl-6-methoxypteridin-7(8H)-one was prepared in the same manner as 4-chloro-8-methyl-6-methoxypteridin-7(8H)-one. The reaction of 6-Chloro-N4-cyclopropyl-pyrimidine-4,5-diamine (3.00 g, 16.2 mmol), methyl 2,2,2-trimethocyacetate (3.73 g, 22.7 mmol), 1-camphorsulfonic acid (0.754 g, 3.25 mmol) in acetonitrile (30 mL) at 80° C. for 16 hours gave 3.045 g of 4-chloro-8-cyclopropyl-6-methoxypteridin-7(8H)-one as a tan colored solid. 1H NMR (400 MHz, DMSO-d6): δ 8.75 (s, 1H), 4.01 (s, 3H), 2.95 (m, 1H), 1.16 (m, 2H), 0.86 (m, 2H). MS (EI) C10H9ClN4O2: 253 (MH+).

Sources & evidence

ORD record
ord-38698f381547465e929676d706e0f839
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

Loading…