6-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione → HCID 59352774, compound

HRID 1407733Notes

Reaction equation

HRID 1407733 reaction equation
Cl[CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1.Br.BrCC1C=CC=CN=1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2([C:32]3=[CH:33][C:34]4[O:38][CH2:37][O:36][C:35]=4[CH:39]=[C:31]3[O:30][CH2:29]2)[C:21]1=[O:40].FC1C2OCCOC=2C=C2OCC3(C4C(=CC=CC=4)NC3=O)C=12>>[O:40]=[C:21]1[C:22]2([C:32]3=[CH:33][C:34]4[O:38][CH2:37][O:36][C:35]=4[CH:39]=[C:31]3[O:30][CH2:29]2)[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:20]1[CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1

Participants

5

Reactant 4

HCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 593527429-fluoro-2,3-dihydro-spiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Product 1

HCID 59352774HCID 59352774, compound

Procedure

Following the procedure as described in EXAMPLE 5.25 and making non-critical variations using 6-(chloromethyl)uracil to replace 2-(bromomethyl)pyridine hydrobromide, and spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 9-fluoro-2,3-dihydro-spiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, 6-[(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)methyl]pyrdimidine-2,4(1H,3H)-dione was obtained (5%) as an off-white solid: mp>300° C.; 1H NMR (300 MHz, DMSO-d6) δ11.11 (s, 1H), 11.05 (s, 1H), 7.29 (dd, J=7.7, 7.7 Hz, 1H), 7.18 (d, J=6.8 Hz, 1H), 7.05 (dd, J=7.5, 7.5 Hz, 1H), 7.03 (dd, J=7.7, 7.7 Hz, 1H), 6.66 (s, 1H), 6.26 (s, 1H), 5.90 (s, 2H), 5.14 (s, 1H), 4.75 (ABq, 2H), 4.60 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ177.4, 164.2, 155.9, 151.8, 151.5, 148.8, 142.3, 142.2, 132.1, 129.4, 124.2, 123.9, 120.1, 109.8, 103.6, 101.9, 96.9, 93.8, 80.4, 57.9, 40.5; MS (ES+) m/z 406.3 (M+1).

Workup

  1. custom6-[(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)methyl]pyrdimidine-2,4(1H,3H)-dione was obtained (5%) as an off-white solid

Sources & evidence

ORD record
ord-0d3343cbacc9430eb5c54540ea3adcea
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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