2,4,5-Trichloropyrimidine → 2-[1-(2,5-Dichloro-pyrimidin-4-ylamino)-cyclohexyl]-acetamide

HRID 1041132Notes

Reaction equation

HRID 1041132 reaction equation
[NH2:1][C:2]1([CH2:8][C:9]([NH2:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([Cl:20])=[CH:15][N:14]=1>>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C:2]2([CH2:8][C:9]([NH2:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:16]([Cl:20])=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 2372592,4,5-TrichloropyrimidineHCID 106070152-(1-Aminocyclohexyl)acetamide

Product 1

HCID 866339402-[1-(2,5-Dichloro-pyrimidin-4-ylamino)-cyclohexyl]-acetamide

Procedure

2-[1-(2,5-Dichloro-pyrimidin-4-ylamino)-cyclohexyl]-acetamide was prepared from 2-(1-Amino-cyclohexyl)-acetamide (2.0 g, 0.013 mol) (Suzuki, T.; Imanishi, N. Itahana, H.; Watauki, S.; Ohta, M.; Mase, T., Synthetic Communications, 1988, 28(4), 701-712) and 2,4,5-Trichloro-pyrimidine (1.5 mL, 0.013 mol) in an analogous manner to Example 1d. Product isolated as a white solid (2.28 g, 59%). MP: 124-128° C. 1HNMR (400 MHz, DMSO-d6, δ, ppm): 8.19 (s, 1H), 7.51 (br s, 1H), 7.34 (br s, 1H), 7.04 (br s, 1H), 2.62 (s, 2H), 2.58-2.52 (m, 2H), 1.55-1.30 (m, 8H). MS: 303.00 (MH)+.

Sources & evidence

ORD record
ord-99dbe5eb23e94ca880d39aafe94b7beb
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…